NPASS Compound

Structure

NPC307883 OpenBabel07101719512D 30 32 0 0 1 0 0 0 0 0999 V2000 -5.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5981 0.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5981 -4.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 0.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 -0.6340 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5981 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5981 -3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0981 -4.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 5 28 1 0 0 0 0 6 10 1 0 0 0 0 6 17 1 0 0 0 0 7 9 2 0 0 0 0 7 18 1 0 0 0 0 8 12 2 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 24 1 0 0 0 0 13 23 1 0 0 0 0 14 19 2 0 0 0 0 14 22 1 0 0 0 0 15 25 1 0 0 0 0 15 29 1 0 0 0 0 16 20 2 0 0 0 0 17 25 1 6 0 0 0 18 22 2 0 0 0 0 19 29 1 0 0 0 0 20 21 1 0 0 0 0 21 25 1 1 0 0 0 22 30 1 0 0 0 0 23 26 2 0 0 0 0 23 28 1 0 0 0 0 24 27 2 0 0 0 0 24 30 1 0 0 0 0 25 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.22
Volume:	440.783
LogP:	5.445
LogD:	4.352
LogS:	-5.735
# Rotatable Bonds:	7
TPSA:	65.74
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.355
Synthetic Accessibility Score:	3.863
Fsp3:	0.52
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.682
MDCK Permeability:	2.343219421163667e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.04
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.843
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	95.27247619628906%
Volume Distribution (VD):	1.684
Pgp-substrate:	4.319660663604736%

ADMET: Metabolism

CYP1A2-inhibitor:	0.844
CYP1A2-substrate:	0.582
CYP2C19-inhibitor:	0.798
CYP2C19-substrate:	0.517
CYP2C9-inhibitor:	0.882
CYP2C9-substrate:	0.585
CYP2D6-inhibitor:	0.649
CYP2D6-substrate:	0.543
CYP3A4-inhibitor:	0.932
CYP3A4-substrate:	0.562

ADMET: Excretion

Clearance (CL):	13.893
Half-life (T1/2):	0.138

ADMET: Toxicity

hERG Blockers:	0.377
Human Hepatotoxicity (H-HT):	0.362
Drug-inuced Liver Injury (DILI):	0.848
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.194
Maximum Recommended Daily Dose:	0.686
Skin Sensitization:	0.235
Carcinogencity:	0.8
Eye Corrosion:	0.004
Eye Irritation:	0.026
Respiratory Toxicity:	0.881

Download Data

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

Natural Product: NPC307883

Natural Product ID:	NPC307883
*Common Name:**	Methyl Galbanate
IUPAC Name:	methyl 3-[(1S,2S,3S)-2,3-dimethyl-2-[(2-oxochromen-7-yl)oxymethyl]-6-propan-2-ylidenecyclohexyl]propanoate
Synonyms:	Methyl Galbanate
Standard InCHIKey:	LWKZASDDSMSRFV-ADSMNUKGSA-N
Standard InCHI:	InChI=1S/C25H32O5/c1-16(2)20-10-6-17(3)25(4,21(20)11-13-23(26)28-5)15-29-19-9-7-18-8-12-24(27)30-22(18)14-19/h7-9,12,14,17,21H,6,10-11,13,15H2,1-5H3/t17-,21-,25-/m0/s1
SMILES:	CC(=C1CC[C@H](C)[C@](C)(COc2ccc3ccc(=O)oc3c2)[C@H]1CCC(=O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078629
PubChem CID:	7075765
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene 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
NPO10996	Ferula assa-foetida	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19691312]
NPO10996	Ferula assa-foetida	Species	Apiaceae	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	7
Others	1

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	8.42	ug.mL-1	PMID[475118]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[475118]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[475118]
NPT1031	Cell Line	Ca9-22	Homo sapiens	IC50	=	19.08	ug.mL-1	PMID[475118]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[475118]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	0.26	ug.mL-1	PMID[475118]
NPT742	Organism	Influenza A virus	Influenza A virus	IC90	=	0.44	ug.mL-1	PMID[475118]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4.33	ug.mL-1	PMID[475118]

☑ 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 NPC307883 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	430
0.1-0.2	1540
0.2-0.3	3366
0.3-0.4	7707
0.4-0.5	10838
0.5-0.6	4813
0.6-0.7	5959
0.7-0.8	6164
0.8-0.85	1457
0.85-0.9	383
0.9-0.95	36
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9701	High Similarity	NPC155552
0.9489	High Similarity	NPC251372
0.9333	High Similarity	NPC306365
0.9155	High Similarity	NPC146388
0.9091	High Similarity	NPC146014
0.9051	High Similarity	NPC131198
0.9044	High Similarity	NPC229128
0.9037	High Similarity	NPC55147
0.9037	High Similarity	NPC54503
0.9007	High Similarity	NPC71739
0.8993	High Similarity	NPC138149
0.8993	High Similarity	NPC472523
0.8929	High Similarity	NPC93640
0.8929	High Similarity	NPC20631
0.8913	High Similarity	NPC14697
0.8905	High Similarity	NPC61499
0.8864	High Similarity	NPC471828
0.8864	High Similarity	NPC471827
0.8841	High Similarity	NPC160727
0.8841	High Similarity	NPC128529
0.8841	High Similarity	NPC471630
0.8841	High Similarity	NPC283331
0.8841	High Similarity	NPC55615
0.8841	High Similarity	NPC283019
0.8841	High Similarity	NPC149320
0.8841	High Similarity	NPC177281
0.8841	High Similarity	NPC476455
0.8824	High Similarity	NPC175159
0.8806	High Similarity	NPC157212
0.8806	High Similarity	NPC472519
0.8788	High Similarity	NPC201667
0.8788	High Similarity	NPC27671
0.8788	High Similarity	NPC73413
0.8777	High Similarity	NPC471068
0.8777	High Similarity	NPC471069
0.8768	High Similarity	NPC86892
0.8768	High Similarity	NPC472424
0.8768	High Similarity	NPC471625
0.8768	High Similarity	NPC471909
0.8768	High Similarity	NPC281241
0.875	High Similarity	NPC472517
0.8731	High Similarity	NPC289316
0.8723	High Similarity	NPC183642
0.8723	High Similarity	NPC136095
0.8723	High Similarity	NPC310370
0.8714	High Similarity	NPC471070
0.8714	High Similarity	NPC471071
0.8714	High Similarity	NPC471072
0.8712	High Similarity	NPC315807
0.8712	High Similarity	NPC109675
0.8712	High Similarity	NPC472518
0.8712	High Similarity	NPC273772
0.8696	High Similarity	NPC84894
0.8696	High Similarity	NPC260265
0.8696	High Similarity	NPC267412
0.8696	High Similarity	NPC198381
0.8696	High Similarity	NPC166672
0.8696	High Similarity	NPC164269
0.8696	High Similarity	NPC100986
0.8696	High Similarity	NPC287182
0.8696	High Similarity	NPC195343
0.8696	High Similarity	NPC47163
0.8696	High Similarity	NPC319859
0.8696	High Similarity	NPC127888
0.8696	High Similarity	NPC74655
0.8696	High Similarity	NPC18804
0.869	High Similarity	NPC142863
0.8686	High Similarity	NPC19157
0.8657	High Similarity	NPC163248
0.8657	High Similarity	NPC471826
0.8657	High Similarity	NPC101894
0.8652	High Similarity	NPC71903
0.8652	High Similarity	NPC36414
0.8643	High Similarity	NPC472516
0.8636	High Similarity	NPC248429
0.8636	High Similarity	NPC96286
0.8633	High Similarity	NPC66705
0.8626	High Similarity	NPC163200
0.8626	High Similarity	NPC235190
0.8626	High Similarity	NPC180006
0.8623	High Similarity	NPC318400
0.8623	High Similarity	NPC133956
0.8623	High Similarity	NPC296624
0.8623	High Similarity	NPC207002
0.8623	High Similarity	NPC167111
0.8623	High Similarity	NPC7526
0.8623	High Similarity	NPC222036
0.8623	High Similarity	NPC471910
0.8611	High Similarity	NPC295696
0.8603	High Similarity	NPC168710
0.8601	High Similarity	NPC229916
0.8592	High Similarity	NPC170812
0.8592	High Similarity	NPC472515
0.8592	High Similarity	NPC473209
0.8582	High Similarity	NPC103001
0.8582	High Similarity	NPC253616
0.8571	High Similarity	NPC104796
0.8561	High Similarity	NPC55149
0.8561	High Similarity	NPC307412
0.8551	High Similarity	NPC280476
0.8551	High Similarity	NPC14248
0.8551	High Similarity	NPC119985
0.854	High Similarity	NPC80170
0.8529	High Similarity	NPC199204
0.8529	High Similarity	NPC185066
0.8519	High Similarity	NPC234109
0.8519	High Similarity	NPC188327
0.8511	High Similarity	NPC254741
0.8511	High Similarity	NPC268081
0.8507	High Similarity	NPC291899
0.8507	High Similarity	NPC111347
0.8493	Intermediate Similarity	NPC286038
0.8489	Intermediate Similarity	NPC469952
0.8489	Intermediate Similarity	NPC83535
0.8489	Intermediate Similarity	NPC469955
0.8489	Intermediate Similarity	NPC31849
0.8489	Intermediate Similarity	NPC472524
0.8477	Intermediate Similarity	NPC474983
0.8473	Intermediate Similarity	NPC298796
0.8473	Intermediate Similarity	NPC281356
0.8467	Intermediate Similarity	NPC474289
0.8462	Intermediate Similarity	NPC287286
0.8456	Intermediate Similarity	NPC189773
0.8451	Intermediate Similarity	NPC319870
0.8451	Intermediate Similarity	NPC148738
0.8451	Intermediate Similarity	NPC327612
0.8451	Intermediate Similarity	NPC211110
0.8451	Intermediate Similarity	NPC73078
0.8446	Intermediate Similarity	NPC103116
0.8435	Intermediate Similarity	NPC66991
0.8433	Intermediate Similarity	NPC290605
0.8433	Intermediate Similarity	NPC173350
0.8433	Intermediate Similarity	NPC50720
0.8433	Intermediate Similarity	NPC154176
0.8421	Intermediate Similarity	NPC144418
0.8417	Intermediate Similarity	NPC469956
0.8406	Intermediate Similarity	NPC32463
0.8403	Intermediate Similarity	NPC46180
0.8397	Intermediate Similarity	NPC96705
0.8397	Intermediate Similarity	NPC265547
0.8397	Intermediate Similarity	NPC152306
0.8394	Intermediate Similarity	NPC139595
0.8394	Intermediate Similarity	NPC293642
0.8394	Intermediate Similarity	NPC469453
0.8394	Intermediate Similarity	NPC60704
0.8392	Intermediate Similarity	NPC312881
0.838	Intermediate Similarity	NPC155963
0.8369	Intermediate Similarity	NPC469675
0.8367	Intermediate Similarity	NPC181388
0.8367	Intermediate Similarity	NPC470322
0.8367	Intermediate Similarity	NPC154217
0.8358	Intermediate Similarity	NPC13007
0.8358	Intermediate Similarity	NPC257188
0.8358	Intermediate Similarity	NPC150214
0.8356	Intermediate Similarity	NPC108994
0.8356	Intermediate Similarity	NPC106126
0.8356	Intermediate Similarity	NPC43716
0.8356	Intermediate Similarity	NPC101255
0.8356	Intermediate Similarity	NPC475719
0.8355	Intermediate Similarity	NPC470625
0.8345	Intermediate Similarity	NPC267336
0.8345	Intermediate Similarity	NPC183646
0.8345	Intermediate Similarity	NPC24075
0.8345	Intermediate Similarity	NPC119640
0.8345	Intermediate Similarity	NPC37009
0.8345	Intermediate Similarity	NPC272650
0.8345	Intermediate Similarity	NPC66430
0.8333	Intermediate Similarity	NPC195357
0.8333	Intermediate Similarity	NPC152771
0.8322	Intermediate Similarity	NPC221046
0.8322	Intermediate Similarity	NPC151946
0.8322	Intermediate Similarity	NPC38153
0.8322	Intermediate Similarity	NPC474305
0.8322	Intermediate Similarity	NPC279573
0.8321	Intermediate Similarity	NPC121740
0.8321	Intermediate Similarity	NPC243688
0.8321	Intermediate Similarity	NPC224774
0.8321	Intermediate Similarity	NPC258567
0.8311	Intermediate Similarity	NPC282335
0.8311	Intermediate Similarity	NPC243154
0.8311	Intermediate Similarity	NPC218300
0.831	Intermediate Similarity	NPC317045
0.831	Intermediate Similarity	NPC246177
0.831	Intermediate Similarity	NPC223616
0.831	Intermediate Similarity	NPC26954
0.831	Intermediate Similarity	NPC38099
0.8299	Intermediate Similarity	NPC208584
0.8299	Intermediate Similarity	NPC1886
0.8299	Intermediate Similarity	NPC178627
0.8299	Intermediate Similarity	NPC469935
0.8299	Intermediate Similarity	NPC294365
0.8299	Intermediate Similarity	NPC196137
0.8299	Intermediate Similarity	NPC171656
0.8298	Intermediate Similarity	NPC326600
0.8298	Intermediate Similarity	NPC180716
0.8298	Intermediate Similarity	NPC62366
0.8298	Intermediate Similarity	NPC131950
0.8298	Intermediate Similarity	NPC50896
0.8298	Intermediate Similarity	NPC204353
0.8298	Intermediate Similarity	NPC213173

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 NPC307883 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	368
0.1-0.2	925
0.2-0.3	1578
0.3-0.4	2535
0.4-0.5	2121
0.5-0.6	1065
0.6-0.7	387
0.7-0.8	131
0.8-0.85	28
0.85-0.9	12
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8705	High Similarity	NPD3748	Approved
0.854	High Similarity	NPD6859	Clinical (unspecified phase)
0.8531	High Similarity	NPD6398	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD3750	Approved
0.838	Intermediate Similarity	NPD2796	Approved
0.8344	Intermediate Similarity	NPD7819	Suspended
0.8309	Intermediate Similarity	NPD2797	Approved
0.8309	Intermediate Similarity	NPD3266	Approved
0.8309	Intermediate Similarity	NPD3267	Approved
0.8273	Intermediate Similarity	NPD1296	Phase 2
0.8146	Intermediate Similarity	NPD6599	Discontinued
0.8143	Intermediate Similarity	NPD3268	Approved
0.8129	Intermediate Similarity	NPD6832	Phase 2
0.8117	Intermediate Similarity	NPD7768	Phase 2
0.8105	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD5124	Phase 1
0.8085	Intermediate Similarity	NPD8032	Phase 2
0.8015	Intermediate Similarity	NPD422	Phase 1
0.8	Intermediate Similarity	NPD6099	Approved
0.8	Intermediate Similarity	NPD6100	Approved
0.7987	Intermediate Similarity	NPD6799	Approved
0.7974	Intermediate Similarity	NPD7411	Suspended
0.7959	Intermediate Similarity	NPD1243	Approved
0.7959	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD7075	Discontinued
0.7947	Intermediate Similarity	NPD920	Approved
0.7933	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD6801	Discontinued
0.7919	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD4628	Phase 3
0.7902	Intermediate Similarity	NPD4307	Phase 2
0.7891	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD4908	Phase 1
0.7857	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD6355	Discontinued
0.7821	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD1510	Phase 2
0.7808	Intermediate Similarity	NPD2799	Discontinued
0.777	Intermediate Similarity	NPD1549	Phase 2
0.7763	Intermediate Similarity	NPD6273	Approved
0.7755	Intermediate Similarity	NPD1551	Phase 2
0.7754	Intermediate Similarity	NPD1610	Phase 2
0.775	Intermediate Similarity	NPD7229	Phase 3
0.7737	Intermediate Similarity	NPD17	Approved
0.773	Intermediate Similarity	NPD5844	Phase 1
0.7714	Intermediate Similarity	NPD3225	Approved
0.7712	Intermediate Similarity	NPD5403	Approved
0.7707	Intermediate Similarity	NPD3817	Phase 2
0.7707	Intermediate Similarity	NPD4288	Approved
0.7703	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5401	Approved
0.7697	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD8127	Discontinued
0.7687	Intermediate Similarity	NPD4308	Phase 3
0.7669	Intermediate Similarity	NPD5535	Approved
0.7667	Intermediate Similarity	NPD7003	Approved
0.7664	Intermediate Similarity	NPD5585	Approved
0.7664	Intermediate Similarity	NPD5691	Approved
0.7654	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD6798	Discontinued
0.7639	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD5494	Approved
0.7613	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD1241	Discontinued
0.761	Intermediate Similarity	NPD3749	Approved
0.7603	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1652	Phase 2
0.7591	Intermediate Similarity	NPD1548	Phase 1
0.7578	Intermediate Similarity	NPD7199	Phase 2
0.7571	Intermediate Similarity	NPD1608	Approved
0.7568	Intermediate Similarity	NPD7033	Discontinued
0.7564	Intermediate Similarity	NPD4380	Phase 2
0.7562	Intermediate Similarity	NPD919	Approved
0.755	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1240	Approved
0.7534	Intermediate Similarity	NPD2979	Phase 3
0.7534	Intermediate Similarity	NPD4140	Approved
0.7532	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4477	Approved
0.7517	Intermediate Similarity	NPD2935	Discontinued
0.7517	Intermediate Similarity	NPD2313	Discontinued
0.7517	Intermediate Similarity	NPD4476	Approved
0.7516	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1281	Approved
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5402	Approved
0.7483	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1019	Discontinued
0.7483	Intermediate Similarity	NPD2798	Approved
0.7482	Intermediate Similarity	NPD1778	Approved
0.7481	Intermediate Similarity	NPD3134	Approved
0.7468	Intermediate Similarity	NPD2532	Approved
0.7468	Intermediate Similarity	NPD37	Approved
0.7468	Intermediate Similarity	NPD2534	Approved
0.7468	Intermediate Similarity	NPD2533	Approved
0.7467	Intermediate Similarity	NPD6002	Phase 3
0.7467	Intermediate Similarity	NPD6005	Phase 3
0.7467	Intermediate Similarity	NPD6004	Phase 3
0.7467	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD8651	Approved
0.7448	Intermediate Similarity	NPD7095	Approved
0.7447	Intermediate Similarity	NPD9717	Approved
0.7447	Intermediate Similarity	NPD3972	Approved
0.7438	Intermediate Similarity	NPD4967	Phase 2
0.7438	Intermediate Similarity	NPD4966	Approved
0.7438	Intermediate Similarity	NPD4965	Approved
0.7432	Intermediate Similarity	NPD1607	Approved
0.7415	Intermediate Similarity	NPD4060	Phase 1
0.7413	Intermediate Similarity	NPD1203	Approved
0.7405	Intermediate Similarity	NPD9697	Approved
0.74	Intermediate Similarity	NPD2438	Suspended
0.7394	Intermediate Similarity	NPD7473	Discontinued
0.7394	Intermediate Similarity	NPD4359	Approved
0.7394	Intermediate Similarity	NPD5327	Phase 3
0.7389	Intermediate Similarity	NPD3226	Approved
0.7376	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2800	Approved
0.7365	Intermediate Similarity	NPD4618	Approved
0.7365	Intermediate Similarity	NPD1933	Approved
0.7365	Intermediate Similarity	NPD4622	Approved
0.7358	Intermediate Similarity	NPD1934	Approved
0.7357	Intermediate Similarity	NPD4626	Approved
0.7351	Intermediate Similarity	NPD2346	Discontinued
0.7351	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6233	Phase 2
0.7346	Intermediate Similarity	NPD6234	Discontinued
0.7343	Intermediate Similarity	NPD1283	Approved
0.7343	Intermediate Similarity	NPD1876	Approved
0.7338	Intermediate Similarity	NPD6667	Approved
0.7338	Intermediate Similarity	NPD1894	Discontinued
0.7338	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6666	Approved
0.7329	Intermediate Similarity	NPD4625	Phase 3
0.732	Intermediate Similarity	NPD4110	Phase 3
0.732	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD8166	Discontinued
0.7317	Intermediate Similarity	NPD6232	Discontinued
0.7315	Intermediate Similarity	NPD6651	Approved
0.7312	Intermediate Similarity	NPD2801	Approved
0.7312	Intermediate Similarity	NPD8455	Phase 2
0.7312	Intermediate Similarity	NPD1465	Phase 2
0.7305	Intermediate Similarity	NPD3496	Discontinued
0.7305	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1358	Approved
0.729	Intermediate Similarity	NPD1511	Approved
0.7286	Intermediate Similarity	NPD1651	Approved
0.7285	Intermediate Similarity	NPD2531	Phase 2
0.7284	Intermediate Similarity	NPD6971	Discontinued
0.7279	Intermediate Similarity	NPD3764	Approved
0.7273	Intermediate Similarity	NPD4749	Approved
0.7267	Intermediate Similarity	NPD7097	Phase 1
0.7267	Intermediate Similarity	NPD5689	Approved
0.7267	Intermediate Similarity	NPD5688	Approved
0.726	Intermediate Similarity	NPD2614	Approved
0.7256	Intermediate Similarity	NPD6959	Discontinued
0.7254	Intermediate Similarity	NPD1611	Approved
0.7246	Intermediate Similarity	NPD7157	Approved
0.7237	Intermediate Similarity	NPD5763	Approved
0.7237	Intermediate Similarity	NPD5762	Approved
0.7229	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3882	Suspended
0.7219	Intermediate Similarity	NPD5953	Discontinued
0.7215	Intermediate Similarity	NPD1653	Approved
0.7208	Intermediate Similarity	NPD7466	Approved
0.7202	Intermediate Similarity	NPD7286	Phase 2
0.7197	Intermediate Similarity	NPD1512	Approved
0.719	Intermediate Similarity	NPD4534	Discontinued
0.719	Intermediate Similarity	NPD2897	Discontinued
0.7176	Intermediate Similarity	NPD6559	Discontinued
0.7162	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7427	Discontinued
0.7143	Intermediate Similarity	NPD3818	Discontinued
0.7143	Intermediate Similarity	NPD7228	Approved
0.7135	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4340	Discontinued
0.7114	Intermediate Similarity	NPD4062	Phase 3
0.7114	Intermediate Similarity	NPD4870	Approved
0.7114	Intermediate Similarity	NPD6663	Approved
0.7108	Intermediate Similarity	NPD7315	Approved
0.7101	Intermediate Similarity	NPD7054	Approved
0.7092	Intermediate Similarity	NPD9545	Approved
0.7089	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5889	Approved
0.7081	Intermediate Similarity	NPD5890	Approved
0.7081	Intermediate Similarity	NPD6677	Suspended
0.7075	Intermediate Similarity	NPD2861	Phase 2
0.7075	Intermediate Similarity	NPD5736	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