NPASS Compound

Structure

CID9812 OpenBabel06191715332D 28 30 0 0 1 0 0 0 0 0999 V2000 -1.7096 2.1575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6357 2.7750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4622 -0.1705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6879 1.5499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2829 1.4535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2867 1.6344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7574 0.5863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5648 1.0803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7509 -1.2933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9377 0.4938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7574 -0.1124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4216 -1.4348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0708 0.5863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2634 1.0803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6319 2.5941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8743 -0.2259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3712 -0.2884 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9734 3.3730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1403 0.5681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9723 0.8231 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2634 -0.6064 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6283 -0.7628 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3186 4.3327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9696 3.1921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0081 1.1039 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5324 0.2555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1454 1.2044 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 5 6 1 0 0 0 0 5 10 2 0 0 0 0 6 15 2 0 0 0 0 7 11 1 0 0 0 0 7 14 2 0 0 0 0 8 13 1 0 0 0 0 8 14 1 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 15 18 1 0 0 0 0 16 23 2 0 0 0 0 16 27 1 0 0 0 0 17 20 1 6 0 0 0 17 22 1 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 19 21 1 0 0 0 0 19 26 2 0 0 0 0 19 28 1 0 0 0 0 20 4 1 1 0 0 0 20 28 1 0 0 0 0 21 22 1 1 0 0 0 22 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.19
Volume:	400.321
LogP:	2.484
LogD:	1.28
LogS:	-3.457
# Rotatable Bonds:	5
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.342
Synthetic Accessibility Score:	5.326
Fsp3:	0.591
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.178
MDCK Permeability:	1.7103524442063645e-05
Pgp-inhibitor:	0.323
Pgp-substrate:	0.192
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.691

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.484
Plasma Protein Binding (PPB):	78.9174575805664%
Volume Distribution (VD):	0.267
Pgp-substrate:	17.443395614624023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.234
CYP2C19-inhibitor:	0.116
CYP2C19-substrate:	0.326
CYP2C9-inhibitor:	0.111
CYP2C9-substrate:	0.792
CYP2D6-inhibitor:	0.172
CYP2D6-substrate:	0.159
CYP3A4-inhibitor:	0.426
CYP3A4-substrate:	0.273

ADMET: Excretion

Clearance (CL):	2.142
Half-life (T1/2):	0.336

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.397
Drug-inuced Liver Injury (DILI):	0.553
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.861
Maximum Recommended Daily Dose:	0.083
Skin Sensitization:	0.16
Carcinogencity:	0.906
Eye Corrosion:	0.01
Eye Irritation:	0.04
Respiratory Toxicity:	0.49

Download Data

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

Natural Product: NPC9812

Natural Product ID:	NPC9812
*Common Name:**	Pseudolaric Acid A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GOHMRMDXUXWCDQ-MPVZDDSSSA-N
Standard InCHI:	InChI=1S/C22H28O6/c1-14-7-11-21-12-9-17(22(21,13-8-14)27-16(3)23)20(4,28-19(21)26)10-5-6-15(2)18(24)25/h5-7,10,17H,8-9,11-13H2,1-4H3,(H,24,25)/b10-5+,15-6+/t17-,20+,21+,22-/m0/s1
SMILES:	CC1=CC[C@@]23[C@@](CC1)(OC(=O)C)[C@@H](CC2)[C@@](OC3=O)(C)/C=C/C=C(/C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL222473
PubChem CID:	6436278
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	root bark	n.a.	n.a.	PMID[14527554]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	tuber	n.a.	PMID[15180301]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	bark	n.a.	n.a.	PMID[17291040]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17381154]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	root and trunk bark	n.a.	n.a.	PMID[18078313]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18078313]
NPO385	Bipolaris oryzae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23668986]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25843525]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8377017]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22239	Hibiscus vitifolius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20140	Aloe perryi	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22239	Hibiscus vitifolius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20140	Aloe perryi	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5178	Pelophylax nigromaculatus	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO33269	pseudolarix kaempfri	Species	Pinaceae	Eukaryota	root bark	n.a.	n.a.	Database[Title]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20328	Plumeria acutifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21090	Chrysanthemum ornatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20772	Pedalium murex	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5178	Pelophylax nigromaculatus	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20262	Delia paludosa	Species	Anthomyiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20140	Aloe perryi	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22563	Sclerocarya birrea	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22239	Hibiscus vitifolius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21914	Turnera angustifolia	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22700	Dacrydium comosum	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO385	Bipolaris oryzae	Species	Pleosporaceae	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	6

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	1510.0	nM	PMID[506780]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	820.0	nM	PMID[506781]
NPT27	Others	Unspecified		IC50	>	100000.0	nM	PMID[506780]
NPT27	Others	Unspecified		IC50	=	950.0	nM	PMID[506781]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5700.0	nM	PMID[506781]

☑ 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 NPC9812 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	179
0.1-0.2	989
0.2-0.3	4243
0.3-0.4	9490
0.4-0.5	14254
0.5-0.6	7567
0.6-0.7	5161
0.7-0.8	791
0.8-0.85	11
0.85-0.9	1
0.9-0.95	5
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.978	High Similarity	NPC64742
0.978	High Similarity	NPC244411
0.957	High Similarity	NPC206079
0.957	High Similarity	NPC116139
0.957	High Similarity	NPC62670
0.9468	High Similarity	NPC66110
0.9271	High Similarity	NPC309190
0.9043	High Similarity	NPC47834
0.8854	High Similarity	NPC280963
0.8404	Intermediate Similarity	NPC77337
0.8316	Intermediate Similarity	NPC472705
0.8202	Intermediate Similarity	NPC469617
0.8125	Intermediate Similarity	NPC45579
0.8073	Intermediate Similarity	NPC13710
0.802	Intermediate Similarity	NPC477950
0.802	Intermediate Similarity	NPC475099
0.8018	Intermediate Similarity	NPC470829
0.8018	Intermediate Similarity	NPC473228
0.7921	Intermediate Similarity	NPC469872
0.7921	Intermediate Similarity	NPC469864
0.7917	Intermediate Similarity	NPC212598
0.7912	Intermediate Similarity	NPC47747
0.79	Intermediate Similarity	NPC202705
0.7889	Intermediate Similarity	NPC63445
0.7889	Intermediate Similarity	NPC222210
0.7879	Intermediate Similarity	NPC171395
0.7872	Intermediate Similarity	NPC476628
0.7872	Intermediate Similarity	NPC245434
0.783	Intermediate Similarity	NPC47951
0.7826	Intermediate Similarity	NPC59994
0.7826	Intermediate Similarity	NPC78677
0.7822	Intermediate Similarity	NPC141191
0.781	Intermediate Similarity	NPC476958
0.78	Intermediate Similarity	NPC185553
0.7789	Intermediate Similarity	NPC234038
0.7778	Intermediate Similarity	NPC167219
0.7766	Intermediate Similarity	NPC14575
0.7766	Intermediate Similarity	NPC196487
0.7755	Intermediate Similarity	NPC261607
0.7755	Intermediate Similarity	NPC300312
0.7755	Intermediate Similarity	NPC111114
0.7745	Intermediate Similarity	NPC290802
0.7736	Intermediate Similarity	NPC220155
0.7732	Intermediate Similarity	NPC106040
0.7732	Intermediate Similarity	NPC115179
0.7723	Intermediate Similarity	NPC108475
0.7723	Intermediate Similarity	NPC169205
0.7723	Intermediate Similarity	NPC170143
0.7723	Intermediate Similarity	NPC213947
0.7723	Intermediate Similarity	NPC477949
0.77	Intermediate Similarity	NPC209355
0.77	Intermediate Similarity	NPC469873
0.7692	Intermediate Similarity	NPC329345
0.7692	Intermediate Similarity	NPC475526
0.7692	Intermediate Similarity	NPC476627
0.7692	Intermediate Similarity	NPC183570
0.7692	Intermediate Similarity	NPC72151
0.7692	Intermediate Similarity	NPC473283
0.7692	Intermediate Similarity	NPC280566
0.7684	Intermediate Similarity	NPC471185
0.7677	Intermediate Similarity	NPC476049
0.7658	Intermediate Similarity	NPC476959
0.7653	Intermediate Similarity	NPC145666
0.7653	Intermediate Similarity	NPC472866
0.7629	Intermediate Similarity	NPC58532
0.7629	Intermediate Similarity	NPC472677
0.7619	Intermediate Similarity	NPC272632
0.7615	Intermediate Similarity	NPC475970
0.7615	Intermediate Similarity	NPC76550
0.7615	Intermediate Similarity	NPC123855
0.7615	Intermediate Similarity	NPC138757
0.7611	Intermediate Similarity	NPC476962
0.7609	Intermediate Similarity	NPC476624
0.7609	Intermediate Similarity	NPC472013
0.7604	Intermediate Similarity	NPC6247
0.7604	Intermediate Similarity	NPC198314
0.7604	Intermediate Similarity	NPC116575
0.76	Intermediate Similarity	NPC65829
0.76	Intermediate Similarity	NPC90453
0.76	Intermediate Similarity	NPC53685
0.7596	Intermediate Similarity	NPC320447
0.7576	Intermediate Similarity	NPC204341
0.7576	Intermediate Similarity	NPC474018
0.7576	Intermediate Similarity	NPC284185
0.7576	Intermediate Similarity	NPC473986
0.7576	Intermediate Similarity	NPC472814
0.7576	Intermediate Similarity	NPC177037
0.7573	Intermediate Similarity	NPC227865
0.7573	Intermediate Similarity	NPC477521
0.7551	Intermediate Similarity	NPC212664
0.7545	Intermediate Similarity	NPC106395
0.7545	Intermediate Similarity	NPC46269
0.7527	Intermediate Similarity	NPC164218
0.7526	Intermediate Similarity	NPC478145
0.7525	Intermediate Similarity	NPC193645
0.7525	Intermediate Similarity	NPC293052
0.7525	Intermediate Similarity	NPC90121
0.7525	Intermediate Similarity	NPC37408
0.7525	Intermediate Similarity	NPC67584
0.7525	Intermediate Similarity	NPC272050
0.7525	Intermediate Similarity	NPC275960
0.7525	Intermediate Similarity	NPC48803
0.7524	Intermediate Similarity	NPC470954
0.7523	Intermediate Similarity	NPC474315
0.75	Intermediate Similarity	NPC146822
0.75	Intermediate Similarity	NPC472871
0.75	Intermediate Similarity	NPC261380
0.75	Intermediate Similarity	NPC469657
0.75	Intermediate Similarity	NPC142649
0.75	Intermediate Similarity	NPC474369
0.75	Intermediate Similarity	NPC244456
0.75	Intermediate Similarity	NPC115021
0.75	Intermediate Similarity	NPC282524
0.75	Intermediate Similarity	NPC169095
0.75	Intermediate Similarity	NPC171759
0.7477	Intermediate Similarity	NPC67290
0.7477	Intermediate Similarity	NPC138303
0.7477	Intermediate Similarity	NPC133677
0.7477	Intermediate Similarity	NPC91034
0.7476	Intermediate Similarity	NPC222011
0.7475	Intermediate Similarity	NPC253144
0.7475	Intermediate Similarity	NPC51486
0.7474	Intermediate Similarity	NPC310470
0.7473	Intermediate Similarity	NPC476317
0.7455	Intermediate Similarity	NPC191620
0.7453	Intermediate Similarity	NPC121099
0.7453	Intermediate Similarity	NPC239162
0.7453	Intermediate Similarity	NPC100487
0.7451	Intermediate Similarity	NPC242848
0.7451	Intermediate Similarity	NPC213078
0.7449	Intermediate Similarity	NPC472870
0.7449	Intermediate Similarity	NPC117122
0.7449	Intermediate Similarity	NPC72397
0.7447	Intermediate Similarity	NPC325031
0.7429	Intermediate Similarity	NPC478156
0.7429	Intermediate Similarity	NPC475091
0.7429	Intermediate Similarity	NPC118405
0.7426	Intermediate Similarity	NPC469632
0.7423	Intermediate Similarity	NPC122502
0.7423	Intermediate Similarity	NPC472869
0.7419	Intermediate Similarity	NPC84185
0.7419	Intermediate Similarity	NPC471890
0.7419	Intermediate Similarity	NPC66677
0.7411	Intermediate Similarity	NPC476963
0.7407	Intermediate Similarity	NPC318363
0.7407	Intermediate Similarity	NPC475418
0.7407	Intermediate Similarity	NPC473482
0.7404	Intermediate Similarity	NPC475053
0.74	Intermediate Similarity	NPC2882
0.74	Intermediate Similarity	NPC70595
0.74	Intermediate Similarity	NPC74103
0.74	Intermediate Similarity	NPC290651
0.74	Intermediate Similarity	NPC150978
0.74	Intermediate Similarity	NPC221282
0.74	Intermediate Similarity	NPC123177
0.7396	Intermediate Similarity	NPC243618
0.7396	Intermediate Similarity	NPC156485
0.7396	Intermediate Similarity	NPC164577
0.7396	Intermediate Similarity	NPC70424
0.7383	Intermediate Similarity	NPC314244
0.7379	Intermediate Similarity	NPC69385
0.7379	Intermediate Similarity	NPC53844
0.7379	Intermediate Similarity	NPC475709
0.7379	Intermediate Similarity	NPC2049
0.7379	Intermediate Similarity	NPC161493
0.7379	Intermediate Similarity	NPC40812
0.7374	Intermediate Similarity	NPC262043
0.7374	Intermediate Similarity	NPC66344
0.7368	Intermediate Similarity	NPC256750
0.7368	Intermediate Similarity	NPC20262
0.7368	Intermediate Similarity	NPC85772
0.7363	Intermediate Similarity	NPC68624
0.7363	Intermediate Similarity	NPC77501
0.7358	Intermediate Similarity	NPC110989
0.7353	Intermediate Similarity	NPC476487
0.7353	Intermediate Similarity	NPC474490
0.7353	Intermediate Similarity	NPC476488
0.7353	Intermediate Similarity	NPC52044
0.7347	Intermediate Similarity	NPC236618
0.7347	Intermediate Similarity	NPC191283
0.7347	Intermediate Similarity	NPC171722
0.7347	Intermediate Similarity	NPC103743
0.7347	Intermediate Similarity	NPC475678
0.7347	Intermediate Similarity	NPC113370
0.7347	Intermediate Similarity	NPC471657
0.7347	Intermediate Similarity	NPC476079
0.7347	Intermediate Similarity	NPC128644
0.7347	Intermediate Similarity	NPC231599
0.7347	Intermediate Similarity	NPC86005
0.7347	Intermediate Similarity	NPC45957
0.7347	Intermediate Similarity	NPC478144
0.7347	Intermediate Similarity	NPC201658
0.7345	Intermediate Similarity	NPC239273
0.7339	Intermediate Similarity	NPC475065
0.7339	Intermediate Similarity	NPC475941
0.7339	Intermediate Similarity	NPC474901
0.7333	Intermediate Similarity	NPC150923
0.7333	Intermediate Similarity	NPC224720
0.7333	Intermediate Similarity	NPC195192
0.7333	Intermediate Similarity	NPC476223

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 NPC9812 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1232
0.2-0.3	3618
0.3-0.4	2733
0.4-0.5	903
0.5-0.6	265
0.6-0.7	213
0.7-0.8	25
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7653	Intermediate Similarity	NPD5785	Approved
0.7525	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6371	Approved
0.7228	Intermediate Similarity	NPD5281	Approved
0.7228	Intermediate Similarity	NPD6411	Approved
0.7228	Intermediate Similarity	NPD5284	Approved
0.7188	Intermediate Similarity	NPD5209	Approved
0.7157	Intermediate Similarity	NPD5779	Approved
0.7157	Intermediate Similarity	NPD5778	Approved
0.7143	Intermediate Similarity	NPD5363	Approved
0.7071	Intermediate Similarity	NPD5786	Approved
0.7059	Intermediate Similarity	NPD5694	Approved
0.7059	Intermediate Similarity	NPD5693	Phase 1
0.7059	Intermediate Similarity	NPD7637	Suspended
0.7043	Intermediate Similarity	NPD7115	Discovery
0.703	Intermediate Similarity	NPD6101	Approved
0.703	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5695	Phase 3
0.701	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5697	Approved
0.6961	Remote Similarity	NPD5207	Approved
0.6961	Remote Similarity	NPD5692	Phase 3
0.6947	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5362	Discontinued
0.6937	Remote Similarity	NPD6899	Approved
0.6937	Remote Similarity	NPD6881	Approved
0.6893	Remote Similarity	NPD6050	Approved
0.6887	Remote Similarity	NPD6084	Phase 2
0.6887	Remote Similarity	NPD6083	Phase 2
0.6875	Remote Similarity	NPD6014	Approved
0.6875	Remote Similarity	NPD6012	Approved
0.6875	Remote Similarity	NPD6013	Approved
0.6847	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6053	Discontinued
0.6837	Remote Similarity	NPD4270	Approved
0.6837	Remote Similarity	NPD6435	Approved
0.6837	Remote Similarity	NPD4269	Approved
0.6822	Remote Similarity	NPD4225	Approved
0.6822	Remote Similarity	NPD5696	Approved
0.6814	Remote Similarity	NPD7102	Approved
0.6814	Remote Similarity	NPD6883	Approved
0.6814	Remote Similarity	NPD7290	Approved
0.6792	Remote Similarity	NPD7839	Suspended
0.6789	Remote Similarity	NPD5211	Phase 2
0.6786	Remote Similarity	NPD6011	Approved
0.6765	Remote Similarity	NPD4518	Approved
0.6757	Remote Similarity	NPD7128	Approved
0.6757	Remote Similarity	NPD6402	Approved
0.6757	Remote Similarity	NPD6675	Approved
0.6757	Remote Similarity	NPD5739	Approved
0.6754	Remote Similarity	NPD6869	Approved
0.6754	Remote Similarity	NPD6649	Approved
0.6754	Remote Similarity	NPD6847	Approved
0.6754	Remote Similarity	NPD6617	Approved
0.6754	Remote Similarity	NPD6650	Approved
0.6754	Remote Similarity	NPD8130	Phase 1
0.6735	Remote Similarity	NPD5369	Approved
0.6733	Remote Similarity	NPD4694	Approved
0.6733	Remote Similarity	NPD5690	Phase 2
0.6733	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5280	Approved
0.6731	Remote Similarity	NPD7983	Approved
0.6699	Remote Similarity	NPD6673	Approved
0.6699	Remote Similarity	NPD6904	Approved
0.6699	Remote Similarity	NPD6080	Approved
0.6696	Remote Similarity	NPD8297	Approved
0.6696	Remote Similarity	NPD5701	Approved
0.6696	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD3573	Approved
0.6637	Remote Similarity	NPD7320	Approved
0.6634	Remote Similarity	NPD1694	Approved
0.6633	Remote Similarity	NPD4822	Approved
0.6633	Remote Similarity	NPD4819	Approved
0.6633	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4821	Approved
0.6633	Remote Similarity	NPD4252	Approved
0.6633	Remote Similarity	NPD4820	Approved
0.6633	Remote Similarity	NPD5368	Approved
0.6632	Remote Similarity	NPD8039	Approved
0.6606	Remote Similarity	NPD7640	Approved
0.6606	Remote Similarity	NPD5285	Approved
0.6606	Remote Similarity	NPD5286	Approved
0.6606	Remote Similarity	NPD4696	Approved
0.6606	Remote Similarity	NPD6404	Discontinued
0.6606	Remote Similarity	NPD7639	Approved
0.6604	Remote Similarity	NPD5282	Discontinued
0.6602	Remote Similarity	NPD5208	Approved
0.66	Remote Similarity	NPD7154	Phase 3
0.6583	Remote Similarity	NPD6319	Approved
0.6579	Remote Similarity	NPD6372	Approved
0.6579	Remote Similarity	NPD6373	Approved
0.656	Remote Similarity	NPD7319	Approved
0.6542	Remote Similarity	NPD5654	Approved
0.6542	Remote Similarity	NPD4629	Approved
0.6542	Remote Similarity	NPD5210	Approved
0.6538	Remote Similarity	NPD4753	Phase 2
0.6535	Remote Similarity	NPD4197	Approved
0.6514	Remote Similarity	NPD7638	Approved
0.6491	Remote Similarity	NPD6686	Approved
0.6486	Remote Similarity	NPD5224	Approved
0.6486	Remote Similarity	NPD4633	Approved
0.6486	Remote Similarity	NPD5225	Approved
0.6486	Remote Similarity	NPD5226	Approved
0.6476	Remote Similarity	NPD46	Approved
0.6476	Remote Similarity	NPD6698	Approved
0.6476	Remote Similarity	NPD4096	Approved
0.6471	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5329	Approved
0.6452	Remote Similarity	NPD7507	Approved
0.6442	Remote Similarity	NPD6672	Approved
0.6442	Remote Similarity	NPD5737	Approved
0.6436	Remote Similarity	NPD5331	Approved
0.6436	Remote Similarity	NPD5332	Approved
0.6429	Remote Similarity	NPD4268	Approved
0.6429	Remote Similarity	NPD5175	Approved
0.6429	Remote Similarity	NPD5174	Approved
0.6429	Remote Similarity	NPD4271	Approved
0.6422	Remote Similarity	NPD4755	Approved
0.6422	Remote Similarity	NPD5959	Approved
0.6415	Remote Similarity	NPD6079	Approved
0.6408	Remote Similarity	NPD6409	Approved
0.6408	Remote Similarity	NPD4689	Approved
0.6408	Remote Similarity	NPD5279	Phase 3
0.6408	Remote Similarity	NPD4690	Approved
0.6408	Remote Similarity	NPD4519	Discontinued
0.6408	Remote Similarity	NPD4138	Approved
0.6408	Remote Similarity	NPD7334	Approved
0.6408	Remote Similarity	NPD4693	Phase 3
0.6408	Remote Similarity	NPD7146	Approved
0.6408	Remote Similarity	NPD5330	Approved
0.6408	Remote Similarity	NPD6098	Approved
0.6408	Remote Similarity	NPD4623	Approved
0.6408	Remote Similarity	NPD6684	Approved
0.6408	Remote Similarity	NPD4688	Approved
0.6408	Remote Similarity	NPD7521	Approved
0.6408	Remote Similarity	NPD5205	Approved
0.64	Remote Similarity	NPD4790	Discontinued
0.6396	Remote Similarity	NPD5223	Approved
0.6389	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6274	Approved
0.6381	Remote Similarity	NPD1695	Approved
0.6379	Remote Similarity	NPD4634	Approved
0.6371	Remote Similarity	NPD7492	Approved
0.6364	Remote Similarity	NPD7100	Approved
0.6364	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4195	Approved
0.6364	Remote Similarity	NPD7101	Approved
0.6356	Remote Similarity	NPD4632	Approved
0.6355	Remote Similarity	NPD6399	Phase 3
0.6337	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6317	Approved
0.633	Remote Similarity	NPD5221	Approved
0.633	Remote Similarity	NPD5222	Approved
0.633	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4756	Discovery
0.6325	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7838	Discovery
0.632	Remote Similarity	NPD6616	Approved
0.6311	Remote Similarity	NPD6054	Approved
0.6306	Remote Similarity	NPD4700	Approved
0.6304	Remote Similarity	NPD7331	Phase 2
0.6296	Remote Similarity	NPD6001	Approved
0.6286	Remote Similarity	NPD6903	Approved
0.6286	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD6335	Approved
0.6281	Remote Similarity	NPD6313	Approved
0.6281	Remote Similarity	NPD6314	Approved
0.6275	Remote Similarity	NPD6695	Phase 3
0.6273	Remote Similarity	NPD5173	Approved
0.627	Remote Similarity	NPD7078	Approved
0.626	Remote Similarity	NPD8513	Phase 3
0.626	Remote Similarity	NPD6015	Approved
0.626	Remote Similarity	NPD6016	Approved
0.626	Remote Similarity	NPD8517	Approved
0.626	Remote Similarity	NPD8515	Approved
0.626	Remote Similarity	NPD8516	Approved
0.626	Remote Similarity	NPD7503	Approved
0.625	Remote Similarity	NPD4249	Approved
0.6226	Remote Similarity	NPD5328	Approved
0.6226	Remote Similarity	NPD6051	Approved
0.622	Remote Similarity	NPD7736	Approved
0.6214	Remote Similarity	NPD3666	Approved
0.6214	Remote Similarity	NPD3665	Phase 1
0.6214	Remote Similarity	NPD3133	Approved
0.6214	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.621	Remote Similarity	NPD5988	Approved
0.621	Remote Similarity	NPD6370	Approved
0.6207	Remote Similarity	NPD4730	Approved
0.6207	Remote Similarity	NPD4729	Approved
0.6204	Remote Similarity	NPD5133	Approved
0.6202	Remote Similarity	NPD7260	Phase 2
0.6198	Remote Similarity	NPD6009	Approved
0.6196	Remote Similarity	NPD7341	Phase 2
0.619	Remote Similarity	NPD4250	Approved
0.619	Remote Similarity	NPD4251	Approved
0.6174	Remote Similarity	NPD6008	Approved
0.6161	Remote Similarity	NPD6648	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