NPASS Compound

Structure

CID204552 OpenBabel06191715592D 29 33 0 0 1 0 0 0 0 0999 V2000 -2.9345 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1748 0.0242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 0.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2613 0.4310 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0685 2.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8005 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 2.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2880 -0.0346 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9345 1.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8040 1.5425 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8495 2.2280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 1.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0685 1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2398 1.1507 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6665 1.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0364 -1.0025 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 0.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6743 1.0500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7772 2.6012 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1478 0.1550 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8918 -0.3369 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3419 2.6909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 8 1 0 0 0 0 4 7 2 0 0 0 0 4 10 1 0 0 0 0 5 9 1 0 0 0 0 5 11 1 0 0 0 0 6 18 1 0 0 0 0 6 28 1 0 0 0 0 7 9 1 0 0 0 0 8 12 1 0 0 0 0 8 19 1 1 0 0 0 9 17 1 6 0 0 0 10 13 1 0 0 0 0 10 21 2 0 0 0 0 11 18 1 1 0 0 0 11 29 1 0 0 0 0 12 20 1 1 0 0 0 12 22 1 0 0 0 0 13 17 1 6 0 0 0 13 23 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 6 0 0 0 14 24 1 0 0 0 0 15 25 2 0 0 0 0 15 29 1 0 0 0 0 16 17 1 6 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 3 1 6 0 0 0 18 19 1 1 0 0 0 19 26 1 6 0 0 0 20 27 1 6 0 0 0 20 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.16
Volume:	382.897
LogP:	0.565
LogD:	-0.276
LogS:	-3.634
# Rotatable Bonds:	0
TPSA:	150.59
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.277
Synthetic Accessibility Score:	6.799
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.462
MDCK Permeability:	4.7640114644309506e-05
Pgp-inhibitor:	0.134
Pgp-substrate:	0.906
Human Intestinal Absorption (HIA):	0.314
20% Bioavailability (F20%):	0.394
30% Bioavailability (F30%):	0.907

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.461
Plasma Protein Binding (PPB):	37.920570373535156%
Volume Distribution (VD):	0.501
Pgp-substrate:	65.92059326171875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.894
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.42
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.051
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.122
CYP3A4-inhibitor:	0.034
CYP3A4-substrate:	0.137

ADMET: Excretion

Clearance (CL):	1.599
Half-life (T1/2):	0.445

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.275
Drug-inuced Liver Injury (DILI):	0.511
AMES Toxicity:	0.068
Rat Oral Acute Toxicity:	0.604
Maximum Recommended Daily Dose:	0.463
Skin Sensitization:	0.337
Carcinogencity:	0.06
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.894

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC204552

Natural Product ID:	NPC204552
*Common Name:**	PKICXNXDFYYYGH-QWRBDCSPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PKICXNXDFYYYGH-QWRBDCSPSA-N
Standard InCHI:	InChI=1S/C20H26O9/c1-7-4-10(21)13(23)17(3)9(7)5-11-18-6-28-20(27,16(17)18)12(22)8(2)19(18,26)14(24)15(25)29-11/h4,8-9,11-14,16,22-24,26-27H,5-6H2,1-3H3/t8-,9-,11+,12+,13+,14-,16+,17+,18+,19-,20-/m0/s1
SMILES:	CC1=CC(=O)[C@H]([C@]2([C@H]1C[C@H]1OC(=O)[C@@H]([C@@]3([C@]41[C@@H]2[C@@](O)(OC4)[C@@H]([C@@H]3C)O)O)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3120500
PubChem CID:	13936707
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828478]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	Roots	n.a.	n.a.	PMID[14575431]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[15520511]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15620254]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1624939]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17027268]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	root	n.a.	PMID[1800638]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO11530	Heterosigma akashiwo	Species	Chattonellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19659728]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19715321]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919052]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19931461]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23403897]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24467387]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[25066952]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25905468]
NPO5401	Monanchora unguiculata	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28368118]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29667820]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1418	Boletinus paluster	Species	Gyrodontaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12577	Pinus glauca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8220	Russula sardonia	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2084	Acinetobacter calcoaceticus	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12988	Blainvillea latifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13692	Leontice kiangnanensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6626	Pteris spinulosa	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20318	Acinetobacter baumannii	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5401	Monanchora unguiculata	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12026	Papaver radicatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11072	Geigeria schinzii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2505	Pachycereus pringlei	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20383	Stenocereus thurberi	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9375	Medium grandiflorum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6014	Goniothalamus undulatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14280	Helichrysum angustifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3576	Bersama swinnyi	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13494	Prosopis kuntzei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13798	Cheilanthes marantae	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3924	Penicillium alutaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22888	Lophiostoma vaginatispora	Species	Lophiostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11530	Heterosigma akashiwo	Species	Chattonellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12890	Ophryosporus charua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9024	Aralidium pinnatifidum	Species	Torricelliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8640	Nemuaron humboldtii	Species	Atherospermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13604	Dermocybe cardinalis	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8820	Lophocereus marginatus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
LD50	1
Others	1

Activity Type	# Activity
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT140	Organism	Artemia	Artemia	LD50	=	10.3	ug ml-1	PMID[455222]
NPT2	Others	Unspecified		IC50	=	700.0	nM	PMID[455222]
NPT2	Others	Unspecified		Inhibition	>	50.0	%	PMID[455222]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC204552 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	1503
0.2-0.3	4524
0.3-0.4	7675
0.4-0.5	11485
0.5-0.6	7851
0.6-0.7	5261
0.7-0.8	3483
0.8-0.85	525
0.85-0.9	72
0.9-0.95	49
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC188667
0.9818	High Similarity	NPC112038
0.973	High Similarity	NPC477046
0.973	High Similarity	NPC102822
0.9727	High Similarity	NPC469488
0.9725	High Similarity	NPC474654
0.9725	High Similarity	NPC287343
0.9725	High Similarity	NPC97908
0.9725	High Similarity	NPC470854
0.9725	High Similarity	NPC122033
0.9636	High Similarity	NPC297179
0.963	High Similarity	NPC208998
0.963	High Similarity	NPC7921
0.9537	High Similarity	NPC11252
0.9537	High Similarity	NPC289312
0.9459	High Similarity	NPC17772
0.9455	High Similarity	NPC235539
0.9455	High Similarity	NPC152199
0.9455	High Similarity	NPC134869
0.945	High Similarity	NPC49451
0.9444	High Similarity	NPC146945
0.9444	High Similarity	NPC171888
0.9444	High Similarity	NPC201992
0.9364	High Similarity	NPC474906
0.9364	High Similarity	NPC18547
0.9286	High Similarity	NPC251310
0.9279	High Similarity	NPC328374
0.9279	High Similarity	NPC96312
0.9279	High Similarity	NPC40632
0.9279	High Similarity	NPC251236
0.9273	High Similarity	NPC51978
0.9204	High Similarity	NPC470777
0.9196	High Similarity	NPC176513
0.9196	High Similarity	NPC470775
0.9189	High Similarity	NPC473798
0.9182	High Similarity	NPC474516
0.9167	High Similarity	NPC293850
0.9138	High Similarity	NPC470922
0.9107	High Similarity	NPC207217
0.9035	High Similarity	NPC475775
0.9035	High Similarity	NPC476529
0.9018	High Similarity	NPC45218
0.9018	High Similarity	NPC323821
0.9018	High Similarity	NPC268238
0.9018	High Similarity	NPC143268
0.9009	High Similarity	NPC302146
0.8974	High Similarity	NPC24651
0.8966	High Similarity	NPC312833
0.8957	High Similarity	NPC107338
0.8957	High Similarity	NPC109607
0.8947	High Similarity	NPC470776
0.8938	High Similarity	NPC16081
0.8938	High Similarity	NPC173686
0.8938	High Similarity	NPC259306
0.8938	High Similarity	NPC470628
0.8938	High Similarity	NPC474046
0.8899	High Similarity	NPC144854
0.8899	High Similarity	NPC3316
0.8889	High Similarity	NPC18945
0.8889	High Similarity	NPC67251
0.8889	High Similarity	NPC105926
0.8889	High Similarity	NPC91693
0.8889	High Similarity	NPC265557
0.886	High Similarity	NPC309433
0.885	High Similarity	NPC470919
0.885	High Similarity	NPC243354
0.885	High Similarity	NPC469877
0.8829	High Similarity	NPC474567
0.8824	High Similarity	NPC470780
0.8818	High Similarity	NPC277017
0.8818	High Similarity	NPC154608
0.8818	High Similarity	NPC192813
0.8814	High Similarity	NPC476729
0.8772	High Similarity	NPC474734
0.8761	High Similarity	NPC194273
0.875	High Similarity	NPC188291
0.875	High Similarity	NPC471243
0.8739	High Similarity	NPC143706
0.8739	High Similarity	NPC225049
0.8739	High Similarity	NPC472534
0.8718	High Similarity	NPC470779
0.8696	High Similarity	NPC473968
0.8696	High Similarity	NPC477116
0.8696	High Similarity	NPC27999
0.8696	High Similarity	NPC473590
0.8689	High Similarity	NPC254614
0.8689	High Similarity	NPC100390
0.8673	High Similarity	NPC472002
0.8636	High Similarity	NPC102352
0.8609	High Similarity	NPC179626
0.8596	High Similarity	NPC194100
0.8596	High Similarity	NPC320118
0.8595	High Similarity	NPC475636
0.8595	High Similarity	NPC295220
0.8583	High Similarity	NPC87662
0.8583	High Similarity	NPC285091
0.8571	High Similarity	NPC227397
0.8547	High Similarity	NPC268958
0.8545	High Similarity	NPC475036
0.8537	High Similarity	NPC254146
0.8537	High Similarity	NPC33378
0.8537	High Similarity	NPC102316
0.8537	High Similarity	NPC6274
0.8525	High Similarity	NPC309096
0.8525	High Similarity	NPC264192
0.8525	High Similarity	NPC54614
0.8522	High Similarity	NPC247069
0.8522	High Similarity	NPC117712
0.8512	High Similarity	NPC476008
0.8509	High Similarity	NPC473397
0.8509	High Similarity	NPC90769
0.85	High Similarity	NPC473255
0.8496	Intermediate Similarity	NPC210005
0.8496	Intermediate Similarity	NPC85391
0.8492	Intermediate Similarity	NPC596
0.8487	Intermediate Similarity	NPC471965
0.8487	Intermediate Similarity	NPC222688
0.848	Intermediate Similarity	NPC262813
0.8468	Intermediate Similarity	NPC181357
0.8468	Intermediate Similarity	NPC168879
0.8435	Intermediate Similarity	NPC471252
0.8435	Intermediate Similarity	NPC255017
0.8435	Intermediate Similarity	NPC477266
0.8435	Intermediate Similarity	NPC198539
0.843	Intermediate Similarity	NPC47113
0.843	Intermediate Similarity	NPC477745
0.843	Intermediate Similarity	NPC174367
0.8421	Intermediate Similarity	NPC213320
0.8421	Intermediate Similarity	NPC29505
0.8417	Intermediate Similarity	NPC14617
0.8417	Intermediate Similarity	NPC478066
0.8417	Intermediate Similarity	NPC262199
0.8417	Intermediate Similarity	NPC202666
0.8417	Intermediate Similarity	NPC471961
0.8417	Intermediate Similarity	NPC471964
0.8413	Intermediate Similarity	NPC243014
0.8413	Intermediate Similarity	NPC190065
0.8413	Intermediate Similarity	NPC251998
0.8413	Intermediate Similarity	NPC471089
0.8413	Intermediate Similarity	NPC141215
0.8407	Intermediate Similarity	NPC218853
0.8407	Intermediate Similarity	NPC141350
0.8403	Intermediate Similarity	NPC75417
0.8403	Intermediate Similarity	NPC275675
0.839	Intermediate Similarity	NPC319570
0.8378	Intermediate Similarity	NPC65523
0.8376	Intermediate Similarity	NPC470778
0.8376	Intermediate Similarity	NPC146432
0.8376	Intermediate Similarity	NPC470171
0.8362	Intermediate Similarity	NPC299849
0.8362	Intermediate Similarity	NPC102088
0.8361	Intermediate Similarity	NPC470882
0.8349	Intermediate Similarity	NPC472972
0.8348	Intermediate Similarity	NPC205534
0.8348	Intermediate Similarity	NPC474927
0.8347	Intermediate Similarity	NPC30188
0.8347	Intermediate Similarity	NPC247315
0.8347	Intermediate Similarity	NPC470477
0.8347	Intermediate Similarity	NPC471962
0.8347	Intermediate Similarity	NPC471963
0.8347	Intermediate Similarity	NPC177820
0.8346	Intermediate Similarity	NPC140045
0.8346	Intermediate Similarity	NPC295885
0.8333	Intermediate Similarity	NPC320383
0.8333	Intermediate Similarity	NPC474786
0.8333	Intermediate Similarity	NPC137104
0.8333	Intermediate Similarity	NPC40775
0.8333	Intermediate Similarity	NPC471093
0.8333	Intermediate Similarity	NPC107966
0.8333	Intermediate Similarity	NPC249848
0.8333	Intermediate Similarity	NPC235438
0.832	Intermediate Similarity	NPC478151
0.8319	Intermediate Similarity	NPC94942
0.8319	Intermediate Similarity	NPC471094
0.8319	Intermediate Similarity	NPC63841
0.8319	Intermediate Similarity	NPC473410
0.8319	Intermediate Similarity	NPC472004
0.8319	Intermediate Similarity	NPC469984
0.8319	Intermediate Similarity	NPC471406
0.8306	Intermediate Similarity	NPC329993
0.8306	Intermediate Similarity	NPC475377
0.8306	Intermediate Similarity	NPC262796
0.8306	Intermediate Similarity	NPC478065
0.8306	Intermediate Similarity	NPC264566
0.8306	Intermediate Similarity	NPC172374
0.8306	Intermediate Similarity	NPC173435
0.8306	Intermediate Similarity	NPC476074
0.8306	Intermediate Similarity	NPC478064
0.8306	Intermediate Similarity	NPC134914
0.8306	Intermediate Similarity	NPC301639
0.8306	Intermediate Similarity	NPC45346
0.8306	Intermediate Similarity	NPC475167
0.8305	Intermediate Similarity	NPC286347
0.8293	Intermediate Similarity	NPC311534
0.8291	Intermediate Similarity	NPC190185
0.8291	Intermediate Similarity	NPC213084
0.8291	Intermediate Similarity	NPC89929
0.8288	Intermediate Similarity	NPC474575
0.8288	Intermediate Similarity	NPC275583
0.8279	Intermediate Similarity	NPC181999

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC204552 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	1745
0.2-0.3	3857
0.3-0.4	2095
0.4-0.5	667
0.5-0.6	299
0.6-0.7	138
0.7-0.8	118
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8417	Intermediate Similarity	NPD8328	Phase 3
0.8319	Intermediate Similarity	NPD6319	Approved
0.8197	Intermediate Similarity	NPD7492	Approved
0.8167	Intermediate Similarity	NPD6059	Approved
0.8167	Intermediate Similarity	NPD6054	Approved
0.8158	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.8145	Intermediate Similarity	NPD7736	Approved
0.813	Intermediate Similarity	NPD6616	Approved
0.8099	Intermediate Similarity	NPD6015	Approved
0.8099	Intermediate Similarity	NPD6016	Approved
0.8067	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD8293	Discontinued
0.8065	Intermediate Similarity	NPD7078	Approved
0.8033	Intermediate Similarity	NPD5988	Approved
0.8033	Intermediate Similarity	NPD6370	Approved
0.7966	Intermediate Similarity	NPD4632	Approved
0.7937	Intermediate Similarity	NPD7319	Approved
0.7917	Intermediate Similarity	NPD6009	Approved
0.7881	Intermediate Similarity	NPD8297	Approved
0.7881	Intermediate Similarity	NPD6882	Approved
0.7826	Intermediate Similarity	NPD6675	Approved
0.7826	Intermediate Similarity	NPD6402	Approved
0.7826	Intermediate Similarity	NPD7128	Approved
0.7826	Intermediate Similarity	NPD5739	Approved
0.7778	Intermediate Similarity	NPD6373	Approved
0.7778	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6372	Approved
0.7778	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD6412	Phase 2
0.7759	Intermediate Similarity	NPD5701	Approved
0.7759	Intermediate Similarity	NPD5697	Approved
0.7712	Intermediate Similarity	NPD4634	Approved
0.7698	Intermediate Similarity	NPD7507	Approved
0.7692	Intermediate Similarity	NPD6881	Approved
0.7692	Intermediate Similarity	NPD6899	Approved
0.7692	Intermediate Similarity	NPD7320	Approved
0.7647	Intermediate Similarity	NPD6650	Approved
0.7647	Intermediate Similarity	NPD6649	Approved
0.7627	Intermediate Similarity	NPD6014	Approved
0.7627	Intermediate Similarity	NPD6013	Approved
0.7627	Intermediate Similarity	NPD6012	Approved
0.7578	Intermediate Similarity	NPD6033	Approved
0.7563	Intermediate Similarity	NPD7102	Approved
0.7563	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD7290	Approved
0.7563	Intermediate Similarity	NPD6883	Approved
0.7542	Intermediate Similarity	NPD6686	Approved
0.7542	Intermediate Similarity	NPD6011	Approved
0.7522	Intermediate Similarity	NPD4755	Approved
0.7521	Intermediate Similarity	NPD6008	Approved
0.752	Intermediate Similarity	NPD5983	Phase 2
0.752	Intermediate Similarity	NPD6921	Approved
0.75	Intermediate Similarity	NPD8130	Phase 1
0.75	Intermediate Similarity	NPD7516	Approved
0.75	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD6869	Approved
0.75	Intermediate Similarity	NPD6617	Approved
0.748	Intermediate Similarity	NPD7115	Discovery
0.7419	Intermediate Similarity	NPD7328	Approved
0.7419	Intermediate Similarity	NPD7327	Approved
0.7402	Intermediate Similarity	NPD7604	Phase 2
0.7391	Intermediate Similarity	NPD4700	Approved
0.7391	Intermediate Similarity	NPD4696	Approved
0.7391	Intermediate Similarity	NPD5285	Approved
0.7391	Intermediate Similarity	NPD5286	Approved
0.7381	Intermediate Similarity	NPD8513	Phase 3
0.7381	Intermediate Similarity	NPD8517	Approved
0.7381	Intermediate Similarity	NPD8515	Approved
0.7381	Intermediate Similarity	NPD8516	Approved
0.7355	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD4225	Approved
0.7287	Intermediate Similarity	NPD6336	Discontinued
0.7265	Intermediate Similarity	NPD5226	Approved
0.7265	Intermediate Similarity	NPD4633	Approved
0.7265	Intermediate Similarity	NPD5224	Approved
0.7265	Intermediate Similarity	NPD5225	Approved
0.7265	Intermediate Similarity	NPD5211	Phase 2
0.7258	Intermediate Similarity	NPD6274	Approved
0.7257	Intermediate Similarity	NPD7748	Approved
0.7232	Intermediate Similarity	NPD7515	Phase 2
0.7227	Intermediate Similarity	NPD4768	Approved
0.7227	Intermediate Similarity	NPD4767	Approved
0.7217	Intermediate Similarity	NPD6083	Phase 2
0.7217	Intermediate Similarity	NPD6084	Phase 2
0.7217	Intermediate Similarity	NPD7902	Approved
0.7203	Intermediate Similarity	NPD5174	Approved
0.7203	Intermediate Similarity	NPD5175	Approved
0.7182	Intermediate Similarity	NPD3573	Approved
0.7179	Intermediate Similarity	NPD5223	Approved
0.7143	Intermediate Similarity	NPD5141	Approved
0.713	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5222	Approved
0.713	Intermediate Similarity	NPD4697	Phase 3
0.713	Intermediate Similarity	NPD5221	Approved
0.7109	Intermediate Similarity	NPD8380	Approved
0.7109	Intermediate Similarity	NPD8379	Approved
0.7109	Intermediate Similarity	NPD8378	Approved
0.7109	Intermediate Similarity	NPD8296	Approved
0.7109	Intermediate Similarity	NPD8033	Approved
0.7109	Intermediate Similarity	NPD8335	Approved
0.7107	Intermediate Similarity	NPD4730	Approved
0.7107	Intermediate Similarity	NPD4729	Approved
0.7105	Intermediate Similarity	NPD5282	Discontinued
0.7097	Intermediate Similarity	NPD8133	Approved
0.7087	Intermediate Similarity	NPD7100	Approved
0.7087	Intermediate Similarity	NPD7101	Approved
0.708	Intermediate Similarity	NPD6411	Approved
0.7069	Intermediate Similarity	NPD5173	Approved
0.7063	Intermediate Similarity	NPD6317	Approved
0.7059	Intermediate Similarity	NPD4754	Approved
0.7054	Intermediate Similarity	NPD5328	Approved
0.7043	Intermediate Similarity	NPD5695	Phase 3
0.7031	Intermediate Similarity	NPD8377	Approved
0.7031	Intermediate Similarity	NPD8294	Approved
0.7018	Intermediate Similarity	NPD6399	Phase 3
0.7009	Intermediate Similarity	NPD7638	Approved
0.7009	Intermediate Similarity	NPD5696	Approved
0.7008	Intermediate Similarity	NPD6335	Approved
0.7008	Intermediate Similarity	NPD6314	Approved
0.7008	Intermediate Similarity	NPD6313	Approved
0.6992	Remote Similarity	NPD5248	Approved
0.6992	Remote Similarity	NPD5249	Phase 3
0.6992	Remote Similarity	NPD5251	Approved
0.6992	Remote Similarity	NPD5250	Approved
0.6992	Remote Similarity	NPD5247	Approved
0.6977	Remote Similarity	NPD6909	Approved
0.6977	Remote Similarity	NPD6908	Approved
0.6977	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7503	Approved
0.697	Remote Similarity	NPD8074	Phase 3
0.6967	Remote Similarity	NPD5128	Approved
0.6957	Remote Similarity	NPD7900	Approved
0.6957	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7640	Approved
0.6949	Remote Similarity	NPD7639	Approved
0.694	Remote Similarity	NPD5956	Approved
0.6937	Remote Similarity	NPD3618	Phase 1
0.6935	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6079	Approved
0.6903	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4753	Phase 2
0.6903	Remote Similarity	NPD6101	Approved
0.687	Remote Similarity	NPD6067	Discontinued
0.687	Remote Similarity	NPD4202	Approved
0.685	Remote Similarity	NPD6868	Approved
0.6814	Remote Similarity	NPD6672	Approved
0.6814	Remote Similarity	NPD5737	Approved
0.68	Remote Similarity	NPD5216	Approved
0.68	Remote Similarity	NPD5217	Approved
0.68	Remote Similarity	NPD5215	Approved
0.675	Remote Similarity	NPD5344	Discontinued
0.6748	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD3667	Approved
0.6724	Remote Similarity	NPD5779	Approved
0.6724	Remote Similarity	NPD5778	Approved
0.672	Remote Similarity	NPD5169	Approved
0.672	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.672	Remote Similarity	NPD5135	Approved
0.6696	Remote Similarity	NPD46	Approved
0.6696	Remote Similarity	NPD6698	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5127	Approved
0.6642	Remote Similarity	NPD7260	Phase 2
0.6638	Remote Similarity	NPD7983	Approved
0.6637	Remote Similarity	NPD5330	Approved
0.6637	Remote Similarity	NPD7146	Approved
0.6637	Remote Similarity	NPD6409	Approved
0.6637	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6684	Approved
0.6637	Remote Similarity	NPD7521	Approved
0.6637	Remote Similarity	NPD7334	Approved
0.6614	Remote Similarity	NPD6053	Discontinued
0.6612	Remote Similarity	NPD1700	Approved
0.661	Remote Similarity	NPD4629	Approved
0.661	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.661	Remote Similarity	NPD5210	Approved
0.6609	Remote Similarity	NPD6673	Approved
0.6609	Remote Similarity	NPD6904	Approved
0.6609	Remote Similarity	NPD6080	Approved
0.6609	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD3665	Phase 1
0.6607	Remote Similarity	NPD3666	Approved
0.6607	Remote Similarity	NPD4786	Approved
0.6607	Remote Similarity	NPD3133	Approved
0.6596	Remote Similarity	NPD6334	Approved
0.6596	Remote Similarity	NPD6333	Approved
0.6587	Remote Similarity	NPD6371	Approved
0.6585	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD4522	Approved
0.656	Remote Similarity	NPD5168	Approved
0.6545	Remote Similarity	NPD4695	Discontinued
0.6541	Remote Similarity	NPD8080	Discontinued
0.6522	Remote Similarity	NPD6903	Approved
0.6512	Remote Similarity	NPD5167	Approved
0.6496	Remote Similarity	NPD8034	Phase 2
0.6496	Remote Similarity	NPD5693	Phase 1
0.6496	Remote Similarity	NPD8035	Phase 2
0.6491	Remote Similarity	NPD5279	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data