NPASS Compound

Structure

NPC118964 OpenBabel07101719252D 36 40 0 0 1 0 0 0 0 0999 V2000 -5.0694 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5103 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0225 -0.6185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8674 -0.8449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2245 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2245 0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6898 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -0.9756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6898 -2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5347 -2.4390 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8449 -2.4390 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5347 2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8449 -1.4634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3796 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5347 1.4634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6898 -3.9024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 -2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8918 -0.8449 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 8 9 1 0 0 0 0 8 17 2 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 10 16 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 27 1 0 0 0 0 13 30 1 0 0 0 0 14 15 1 0 0 0 0 14 26 1 0 0 0 0 15 30 1 0 0 0 0 16 29 1 6 0 0 0 17 21 1 0 0 0 0 17 26 1 0 0 0 0 18 25 1 0 0 0 0 18 28 1 1 0 0 0 19 27 1 1 0 0 0 19 28 1 0 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 20 31 2 0 0 0 0 21 29 1 6 0 0 0 21 30 1 0 0 0 0 22 25 1 0 0 0 0 22 32 1 1 0 0 0 23 28 1 1 0 0 0 23 33 1 0 0 0 0 24 34 2 0 0 0 0 24 35 1 0 0 0 0 26 27 1 1 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 29 7 1 1 0 0 0 29 36 1 0 0 0 0 30 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.33
Volume:	529.486
LogP:	3.833
LogD:	3.315
LogS:	-3.785
# Rotatable Bonds:	1
TPSA:	115.06
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.396
Synthetic Accessibility Score:	5.274
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.702
MDCK Permeability:	1.4396834558283444e-05
Pgp-inhibitor:	0.064
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.064
20% Bioavailability (F20%):	0.064
30% Bioavailability (F30%):	0.45

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.913
Plasma Protein Binding (PPB):	80.19274139404297%
Volume Distribution (VD):	0.424
Pgp-substrate:	21.726924896240234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.396
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.656
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.19
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.199
CYP3A4-substrate:	0.162

ADMET: Excretion

Clearance (CL):	2.642
Half-life (T1/2):	0.169

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.2
Drug-inuced Liver Injury (DILI):	0.062
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.893
Maximum Recommended Daily Dose:	0.875
Skin Sensitization:	0.074
Carcinogencity:	0.44
Eye Corrosion:	0.026
Eye Irritation:	0.035
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC118964

Natural Product ID:	NPC118964
*Common Name:**	1Beta-Hydroxy-2-Oxopomolic Acid
IUPAC Name:	(1R,2R,4aS,6aS,6aS,6bR,8aS,10R,12S,12aR,14bS)-1,10,12-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-11-oxo-3,4,5,6,6a,7,8,8a,10,12,13,14b-dodecahydro-2H-picene-4a-carboxylic acid
Synonyms:
Standard InCHIKey:	VBLIMTVKFVIDFU-PAZRJNPVSA-N
Standard InCHI:	InChI=1S/C30H46O6/c1-16-10-13-30(24(34)35)15-14-26(4)17(21(30)29(16,7)36)8-9-19-27(26,5)12-11-18-25(2,3)22(32)20(31)23(33)28(18,19)6/h8,16,18-19,21-23,32-33,36H,9-15H2,1-7H3,(H,34,35)/t16-,18+,19+,21-,22+,23-,26-,27-,28+,29-,30+/m1/s1
SMILES:	O=C1[C@@H](O)[C@@]2(C)[C@H](C([C@H]1O)(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2[C@](C)(O)[C@H](C)CC1)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461068
PubChem CID:	10625284
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473413]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3613	Eriobotrya deflexa	Species	Rosaceae	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	2

Activity Type	# Activity
NON-MOLECULAR	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	32500.0	nM	PMID[460148]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	40.0	ug.mL-1	PMID[460149]

☑ 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 NPC118964 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	234
0.1-0.2	1508
0.2-0.3	4854
0.3-0.4	10595
0.4-0.5	11550
0.5-0.6	6090
0.6-0.7	5084
0.7-0.8	2316
0.8-0.85	228
0.85-0.9	175
0.9-0.95	60
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.957	High Similarity	NPC62516
0.957	High Similarity	NPC157113
0.9375	High Similarity	NPC256247
0.9355	High Similarity	NPC159365
0.9355	High Similarity	NPC6818
0.9355	High Similarity	NPC114159
0.9355	High Similarity	NPC191412
0.9247	High Similarity	NPC229281
0.9247	High Similarity	NPC118519
0.9247	High Similarity	NPC202728
0.9247	High Similarity	NPC118490
0.9247	High Similarity	NPC158059
0.9158	High Similarity	NPC476318
0.9158	High Similarity	NPC476327
0.9158	High Similarity	NPC132824
0.9158	High Similarity	NPC116457
0.914	High Similarity	NPC187722
0.914	High Similarity	NPC474525
0.914	High Similarity	NPC38754
0.914	High Similarity	NPC105189
0.914	High Similarity	NPC475708
0.9062	High Similarity	NPC43686
0.9062	High Similarity	NPC9613
0.9062	High Similarity	NPC247139
0.9053	High Similarity	NPC473240
0.9032	High Similarity	NPC227467
0.9032	High Similarity	NPC130278
0.9032	High Similarity	NPC273621
0.9032	High Similarity	NPC120968
0.9032	High Similarity	NPC46441
0.9032	High Similarity	NPC470589
0.9032	High Similarity	NPC18872
0.9032	High Similarity	NPC126369
0.9032	High Similarity	NPC290614
0.9032	High Similarity	NPC193750
0.9032	High Similarity	NPC291028
0.9032	High Similarity	NPC111110
0.9032	High Similarity	NPC210037
0.9032	High Similarity	NPC7260
0.9032	High Similarity	NPC477872
0.8969	High Similarity	NPC174663
0.8958	High Similarity	NPC19376
0.8958	High Similarity	NPC327179
0.8958	High Similarity	NPC173744
0.8958	High Similarity	NPC25848
0.8958	High Similarity	NPC73004
0.8958	High Similarity	NPC307282
0.8958	High Similarity	NPC204961
0.8958	High Similarity	NPC259733
0.8958	High Similarity	NPC158371
0.8958	High Similarity	NPC305464
0.8958	High Similarity	NPC207922
0.8947	High Similarity	NPC148964
0.8936	High Similarity	NPC235704
0.8925	High Similarity	NPC293048
0.8925	High Similarity	NPC25906
0.8925	High Similarity	NPC274330
0.8925	High Similarity	NPC263393
0.8925	High Similarity	NPC130520
0.8925	High Similarity	NPC127689
0.8925	High Similarity	NPC198664
0.8925	High Similarity	NPC143232
0.8925	High Similarity	NPC290972
0.8925	High Similarity	NPC61543
0.8925	High Similarity	NPC64872
0.8925	High Similarity	NPC121798
0.8925	High Similarity	NPC59263
0.8925	High Similarity	NPC234346
0.8925	High Similarity	NPC270768
0.8925	High Similarity	NPC225585
0.89	High Similarity	NPC284865
0.8878	High Similarity	NPC35239
0.8866	High Similarity	NPC476878
0.8866	High Similarity	NPC187933
0.8866	High Similarity	NPC189880
0.8866	High Similarity	NPC476879
0.8866	High Similarity	NPC255589
0.8866	High Similarity	NPC259788
0.8854	High Similarity	NPC83693
0.8854	High Similarity	NPC96916
0.8817	High Similarity	NPC290690
0.8817	High Similarity	NPC181225
0.8817	High Similarity	NPC470629
0.8817	High Similarity	NPC17733
0.8817	High Similarity	NPC182797
0.8817	High Similarity	NPC473242
0.8817	High Similarity	NPC474512
0.8817	High Similarity	NPC52169
0.8776	High Similarity	NPC29765
0.8776	High Similarity	NPC111214
0.8776	High Similarity	NPC58942
0.8776	High Similarity	NPC260149
0.8776	High Similarity	NPC271614
0.875	High Similarity	NPC145667
0.875	High Similarity	NPC32407
0.875	High Similarity	NPC231063
0.875	High Similarity	NPC60692
0.875	High Similarity	NPC299996
0.875	High Similarity	NPC263548
0.875	High Similarity	NPC88116
0.875	High Similarity	NPC282395
0.875	High Similarity	NPC20235
0.8737	High Similarity	NPC233455
0.8737	High Similarity	NPC158030
0.8737	High Similarity	NPC966
0.8737	High Similarity	NPC288833
0.8737	High Similarity	NPC145067
0.8737	High Similarity	NPC65120
0.8737	High Similarity	NPC471588
0.8737	High Similarity	NPC324341
0.8737	High Similarity	NPC155120
0.8737	High Similarity	NPC282616
0.8737	High Similarity	NPC4036
0.8737	High Similarity	NPC6255
0.8737	High Similarity	NPC228784
0.8723	High Similarity	NPC470588
0.871	High Similarity	NPC98442
0.871	High Similarity	NPC142415
0.871	High Similarity	NPC73064
0.871	High Similarity	NPC293564
0.871	High Similarity	NPC242468
0.871	High Similarity	NPC171203
0.871	High Similarity	NPC18064
0.871	High Similarity	NPC68160
0.871	High Similarity	NPC307426
0.871	High Similarity	NPC130577
0.871	High Similarity	NPC51700
0.871	High Similarity	NPC88716
0.871	High Similarity	NPC102683
0.87	High Similarity	NPC477054
0.8673	High Similarity	NPC106112
0.8673	High Similarity	NPC261935
0.866	High Similarity	NPC148523
0.866	High Similarity	NPC290481
0.866	High Similarity	NPC139570
0.866	High Similarity	NPC32118
0.866	High Similarity	NPC474727
0.8646	High Similarity	NPC275809
0.8646	High Similarity	NPC272075
0.8646	High Similarity	NPC86368
0.8646	High Similarity	NPC214756
0.8646	High Similarity	NPC295643
0.8632	High Similarity	NPC86372
0.8632	High Similarity	NPC474728
0.8632	High Similarity	NPC172361
0.8627	High Similarity	NPC477877
0.8617	High Similarity	NPC246708
0.8617	High Similarity	NPC40552
0.8602	High Similarity	NPC475862
0.8602	High Similarity	NPC72638
0.8602	High Similarity	NPC74363
0.8602	High Similarity	NPC213412
0.86	High Similarity	NPC54909
0.86	High Similarity	NPC477052
0.86	High Similarity	NPC477053
0.86	High Similarity	NPC477051
0.86	High Similarity	NPC233012
0.8586	High Similarity	NPC164349
0.8571	High Similarity	NPC201657
0.8571	High Similarity	NPC98874
0.8557	High Similarity	NPC80365
0.8557	High Similarity	NPC222047
0.8557	High Similarity	NPC209868
0.8557	High Similarity	NPC474529
0.8542	High Similarity	NPC470590
0.8542	High Similarity	NPC52021
0.8542	High Similarity	NPC300351
0.8542	High Similarity	NPC77099
0.8542	High Similarity	NPC71074
0.8542	High Similarity	NPC235884
0.8542	High Similarity	NPC25299
0.8542	High Similarity	NPC84319
0.8542	High Similarity	NPC472149
0.8542	High Similarity	NPC285184
0.8542	High Similarity	NPC306541
0.8542	High Similarity	NPC60755
0.8526	High Similarity	NPC95246
0.8526	High Similarity	NPC474686
0.8526	High Similarity	NPC474972
0.8526	High Similarity	NPC161751
0.8511	High Similarity	NPC71507
0.8495	Intermediate Similarity	NPC133954
0.8485	Intermediate Similarity	NPC203343
0.8485	Intermediate Similarity	NPC312075
0.8469	Intermediate Similarity	NPC195715
0.8469	Intermediate Similarity	NPC147232
0.8469	Intermediate Similarity	NPC266899
0.8454	Intermediate Similarity	NPC474436
0.8454	Intermediate Similarity	NPC474806
0.8454	Intermediate Similarity	NPC133579
0.8454	Intermediate Similarity	NPC307335
0.8454	Intermediate Similarity	NPC63118
0.8454	Intermediate Similarity	NPC49776
0.8454	Intermediate Similarity	NPC74855
0.8454	Intermediate Similarity	NPC298554
0.8454	Intermediate Similarity	NPC136313
0.8438	Intermediate Similarity	NPC49320
0.8438	Intermediate Similarity	NPC120840
0.8438	Intermediate Similarity	NPC113989
0.8431	Intermediate Similarity	NPC478057

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 NPC118964 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	1831
0.2-0.3	3775
0.3-0.4	2181
0.4-0.5	680
0.5-0.6	224
0.6-0.7	168
0.7-0.8	71
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8737	High Similarity	NPD7515	Phase 2
0.8485	Intermediate Similarity	NPD7902	Approved
0.8367	Intermediate Similarity	NPD7748	Approved
0.8182	Intermediate Similarity	NPD7900	Approved
0.8182	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD5739	Approved
0.7925	Intermediate Similarity	NPD7128	Approved
0.7925	Intermediate Similarity	NPD6675	Approved
0.7925	Intermediate Similarity	NPD6402	Approved
0.79	Intermediate Similarity	NPD6399	Phase 3
0.787	Intermediate Similarity	NPD6373	Approved
0.787	Intermediate Similarity	NPD6372	Approved
0.7778	Intermediate Similarity	NPD6881	Approved
0.7778	Intermediate Similarity	NPD7320	Approved
0.7778	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6899	Approved
0.7767	Intermediate Similarity	NPD4755	Approved
0.7759	Intermediate Similarity	NPD8328	Phase 3
0.7732	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6650	Approved
0.7727	Intermediate Similarity	NPD6649	Approved
0.7699	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD5701	Approved
0.7685	Intermediate Similarity	NPD5697	Approved
0.766	Intermediate Similarity	NPD7645	Phase 2
0.7653	Intermediate Similarity	NPD3618	Phase 1
0.7636	Intermediate Similarity	NPD7102	Approved
0.7636	Intermediate Similarity	NPD6883	Approved
0.7636	Intermediate Similarity	NPD7290	Approved
0.7629	Intermediate Similarity	NPD4786	Approved
0.7624	Intermediate Similarity	NPD8034	Phase 2
0.7624	Intermediate Similarity	NPD8035	Phase 2
0.7619	Intermediate Similarity	NPD5285	Approved
0.7619	Intermediate Similarity	NPD4700	Approved
0.7619	Intermediate Similarity	NPD5286	Approved
0.7619	Intermediate Similarity	NPD4696	Approved
0.7604	Intermediate Similarity	NPD3667	Approved
0.7596	Intermediate Similarity	NPD6083	Phase 2
0.7596	Intermediate Similarity	NPD6084	Phase 2
0.7568	Intermediate Similarity	NPD6869	Approved
0.7568	Intermediate Similarity	NPD6847	Approved
0.7568	Intermediate Similarity	NPD8130	Phase 1
0.7568	Intermediate Similarity	NPD6617	Approved
0.7545	Intermediate Similarity	NPD6014	Approved
0.7545	Intermediate Similarity	NPD6012	Approved
0.7545	Intermediate Similarity	NPD6013	Approved
0.7545	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4697	Phase 3
0.75	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD6882	Approved
0.7477	Intermediate Similarity	NPD5226	Approved
0.7477	Intermediate Similarity	NPD5224	Approved
0.7477	Intermediate Similarity	NPD4633	Approved
0.7477	Intermediate Similarity	NPD5211	Phase 2
0.7477	Intermediate Similarity	NPD5225	Approved
0.7455	Intermediate Similarity	NPD6011	Approved
0.7455	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4632	Approved
0.7426	Intermediate Similarity	NPD4753	Phase 2
0.7426	Intermediate Similarity	NPD5328	Approved
0.7411	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5175	Approved
0.7407	Intermediate Similarity	NPD5174	Approved
0.7383	Intermediate Similarity	NPD5223	Approved
0.7379	Intermediate Similarity	NPD4202	Approved
0.7358	Intermediate Similarity	NPD7638	Approved
0.7358	Intermediate Similarity	NPD5696	Approved
0.7339	Intermediate Similarity	NPD5141	Approved
0.7333	Intermediate Similarity	NPD5221	Approved
0.7333	Intermediate Similarity	NPD5222	Approved
0.7333	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD4634	Approved
0.729	Intermediate Similarity	NPD7640	Approved
0.729	Intermediate Similarity	NPD7639	Approved
0.7282	Intermediate Similarity	NPD6079	Approved
0.7273	Intermediate Similarity	NPD4767	Approved
0.7273	Intermediate Similarity	NPD4768	Approved
0.7273	Intermediate Similarity	NPD6008	Approved
0.7264	Intermediate Similarity	NPD5173	Approved
0.7248	Intermediate Similarity	NPD4754	Approved
0.7241	Intermediate Similarity	NPD6009	Approved
0.7241	Intermediate Similarity	NPD7115	Discovery
0.7238	Intermediate Similarity	NPD5210	Approved
0.7238	Intermediate Similarity	NPD4629	Approved
0.7238	Intermediate Similarity	NPD5695	Phase 3
0.7216	Intermediate Similarity	NPD7525	Registered
0.7216	Intermediate Similarity	NPD4695	Discontinued
0.7213	Intermediate Similarity	NPD7736	Approved
0.7203	Intermediate Similarity	NPD6319	Approved
0.7157	Intermediate Similarity	NPD5737	Approved
0.7157	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD6672	Approved
0.7155	Intermediate Similarity	NPD6274	Approved
0.7143	Intermediate Similarity	NPD5128	Approved
0.7143	Intermediate Similarity	NPD4730	Approved
0.7143	Intermediate Similarity	NPD4729	Approved
0.7119	Intermediate Similarity	NPD7100	Approved
0.7119	Intermediate Similarity	NPD7101	Approved
0.7115	Intermediate Similarity	NPD6411	Approved
0.7107	Intermediate Similarity	NPD7492	Approved
0.71	Intermediate Similarity	NPD3668	Phase 3
0.71	Intermediate Similarity	NPD3665	Phase 1
0.71	Intermediate Similarity	NPD3133	Approved
0.71	Intermediate Similarity	NPD3666	Approved
0.708	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3573	Approved
0.7059	Intermediate Similarity	NPD6059	Approved
0.7059	Intermediate Similarity	NPD6054	Approved
0.7054	Intermediate Similarity	NPD6412	Phase 2
0.7049	Intermediate Similarity	NPD6616	Approved
0.7034	Intermediate Similarity	NPD6335	Approved
0.703	Intermediate Similarity	NPD5329	Approved
0.7025	Intermediate Similarity	NPD7604	Phase 2
0.7018	Intermediate Similarity	NPD5249	Phase 3
0.7018	Intermediate Similarity	NPD5250	Approved
0.7018	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5251	Approved
0.7018	Intermediate Similarity	NPD5247	Approved
0.7018	Intermediate Similarity	NPD5248	Approved
0.701	Intermediate Similarity	NPD6697	Approved
0.701	Intermediate Similarity	NPD6115	Approved
0.701	Intermediate Similarity	NPD6118	Approved
0.701	Intermediate Similarity	NPD6114	Approved
0.7	Intermediate Similarity	NPD6908	Approved
0.7	Intermediate Similarity	NPD5983	Phase 2
0.7	Intermediate Similarity	NPD6909	Approved
0.6992	Remote Similarity	NPD7078	Approved
0.6992	Remote Similarity	NPD8293	Discontinued
0.6961	Remote Similarity	NPD5330	Approved
0.6961	Remote Similarity	NPD7521	Approved
0.6961	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6098	Approved
0.6961	Remote Similarity	NPD7146	Approved
0.6961	Remote Similarity	NPD6684	Approved
0.6961	Remote Similarity	NPD5279	Phase 3
0.6961	Remote Similarity	NPD7334	Approved
0.6961	Remote Similarity	NPD6409	Approved
0.6957	Remote Similarity	NPD5215	Approved
0.6957	Remote Similarity	NPD5216	Approved
0.6957	Remote Similarity	NPD5217	Approved
0.6952	Remote Similarity	NPD5281	Approved
0.6952	Remote Similarity	NPD5284	Approved
0.6949	Remote Similarity	NPD6317	Approved
0.6942	Remote Similarity	NPD6370	Approved
0.6931	Remote Similarity	NPD4197	Approved
0.6923	Remote Similarity	NPD6080	Approved
0.6923	Remote Similarity	NPD6904	Approved
0.6923	Remote Similarity	NPD6101	Approved
0.6923	Remote Similarity	NPD6673	Approved
0.6923	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD6336	Discontinued
0.6907	Remote Similarity	NPD6116	Phase 1
0.6891	Remote Similarity	NPD6314	Approved
0.6891	Remote Similarity	NPD6313	Approved
0.6887	Remote Similarity	NPD5778	Approved
0.6887	Remote Similarity	NPD5779	Approved
0.687	Remote Similarity	NPD5135	Approved
0.687	Remote Similarity	NPD5169	Approved
0.687	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6868	Approved
0.686	Remote Similarity	NPD6015	Approved
0.686	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6016	Approved
0.6852	Remote Similarity	NPD7614	Phase 1
0.6838	Remote Similarity	NPD8133	Approved
0.6827	Remote Similarity	NPD6903	Approved
0.681	Remote Similarity	NPD5127	Approved
0.6804	Remote Similarity	NPD6117	Approved
0.6803	Remote Similarity	NPD5988	Approved
0.6774	Remote Similarity	NPD7507	Approved
0.6754	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7319	Approved
0.6733	Remote Similarity	NPD4221	Approved
0.6733	Remote Similarity	NPD4223	Phase 3
0.6727	Remote Similarity	NPD4225	Approved
0.6721	Remote Similarity	NPD6921	Approved
0.6701	Remote Similarity	NPD7339	Approved
0.6701	Remote Similarity	NPD6942	Approved
0.67	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5168	Approved
0.6696	Remote Similarity	NPD6686	Approved
0.6696	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD3617	Approved
0.6667	Remote Similarity	NPD4788	Approved
0.6667	Remote Similarity	NPD5282	Discontinued
0.6639	Remote Similarity	NPD5167	Approved
0.6636	Remote Similarity	NPD5693	Phase 1
0.6636	Remote Similarity	NPD7637	Suspended
0.6636	Remote Similarity	NPD6050	Approved
0.6635	Remote Similarity	NPD5280	Approved
0.6635	Remote Similarity	NPD4694	Approved
0.6635	Remote Similarity	NPD5690	Phase 2
0.6633	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7328	Approved
0.6612	Remote Similarity	NPD7327	Approved
0.6602	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD8033	Approved
0.6585	Remote Similarity	NPD8379	Approved

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