NPASS Compound

Structure

NPC155552 OpenBabel07101718292D 29 31 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 -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 -5.0981 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 -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 -5.0981 4.0981 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 -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 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 5 9 1 0 0 0 0 5 16 1 0 0 0 0 6 8 2 0 0 0 0 6 17 1 0 0 0 0 7 12 2 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 18 2 0 0 0 0 13 21 1 0 0 0 0 14 24 1 0 0 0 0 14 28 1 0 0 0 0 15 19 2 0 0 0 0 16 24 1 1 0 0 0 17 21 2 0 0 0 0 18 28 1 0 0 0 0 19 20 1 0 0 0 0 20 24 1 6 0 0 0 21 29 1 0 0 0 0 22 25 2 0 0 0 0 22 26 1 0 0 0 0 23 27 2 0 0 0 0 23 29 1 0 0 0 0 24 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.21
Volume:	423.487
LogP:	5.163
LogD:	3.911
LogS:	-4.512
# Rotatable Bonds:	6
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.519
Synthetic Accessibility Score:	3.849
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.881
MDCK Permeability:	2.4492188458680175e-05
Pgp-inhibitor:	0.091
Pgp-substrate:	0.598
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.273
30% Bioavailability (F30%):	0.891

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.035
Plasma Protein Binding (PPB):	96.07357025146484%
Volume Distribution (VD):	0.577
Pgp-substrate:	3.083789587020874%

ADMET: Metabolism

CYP1A2-inhibitor:	0.314
CYP1A2-substrate:	0.467
CYP2C19-inhibitor:	0.22
CYP2C19-substrate:	0.158
CYP2C9-inhibitor:	0.472
CYP2C9-substrate:	0.924
CYP2D6-inhibitor:	0.136
CYP2D6-substrate:	0.5
CYP3A4-inhibitor:	0.144
CYP3A4-substrate:	0.223

ADMET: Excretion

Clearance (CL):	11.282
Half-life (T1/2):	0.506

ADMET: Toxicity

hERG Blockers:	0.08
Human Hepatotoxicity (H-HT):	0.369
Drug-inuced Liver Injury (DILI):	0.653
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.209
Maximum Recommended Daily Dose:	0.585
Skin Sensitization:	0.153
Carcinogencity:	0.799
Eye Corrosion:	0.004
Eye Irritation:	0.039
Respiratory Toxicity:	0.908

Download Data

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

Natural Product: NPC155552

Natural Product ID:	NPC155552
*Common Name:**	Galbanic Acid
IUPAC Name:	3-[(1S,2S,3S)-2,3-dimethyl-2-[(2-oxochromen-7-yl)oxymethyl]-6-propan-2-ylidenecyclohexyl]propanoic acid
Synonyms:	Galbanic Acid
Standard InCHIKey:	CVWWNYPTZYQCSE-YFBXQHAESA-N
Standard InCHI:	InChI=1S/C24H30O5/c1-15(2)19-9-5-16(3)24(4,20(19)10-11-22(25)26)14-28-18-8-6-17-7-12-23(27)29-21(17)13-18/h6-8,12-13,16,20H,5,9-11,14H2,1-4H3,(H,25,26)/t16-,20-,24-/m0/s1
SMILES:	OC(=O)CC[C@H]1C(=C(C)C)CC[C@@H]([C@]1(C)COc1ccc2c(c1)oc(=O)cc2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078509
PubChem CID:	7082474
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	1
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	0.45	ug.mL-1	PMID[527755]
NPT742	Organism	Influenza A virus	Influenza A virus	IC90	=	0.88	ug.mL-1	PMID[527755]

☑ 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 NPC155552 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	360
0.1-0.2	1488
0.2-0.3	3023
0.3-0.4	7262
0.4-0.5	11086
0.5-0.6	4822
0.6-0.7	5873
0.7-0.8	5981
0.8-0.85	2020
0.85-0.9	701
0.9-0.95	74
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9701	High Similarity	NPC307883
0.9433	High Similarity	NPC146388
0.9366	High Similarity	NPC146014
0.9353	High Similarity	NPC251372
0.9338	High Similarity	NPC131198
0.9286	High Similarity	NPC71739
0.9275	High Similarity	NPC138149
0.9209	High Similarity	NPC20631
0.9209	High Similarity	NPC93640
0.9191	High Similarity	NPC61499
0.9058	High Similarity	NPC306365
0.9	High Similarity	NPC183642
0.9	High Similarity	NPC310370
0.8958	High Similarity	NPC142863
0.8929	High Similarity	NPC71903
0.8921	High Similarity	NPC471069
0.8921	High Similarity	NPC471068
0.8913	High Similarity	NPC229128
0.8905	High Similarity	NPC55147
0.8905	High Similarity	NPC54503
0.8881	High Similarity	NPC295696
0.8873	High Similarity	NPC229916
0.8865	High Similarity	NPC170812
0.8865	High Similarity	NPC472523
0.8857	High Similarity	NPC471072
0.8857	High Similarity	NPC471071
0.8857	High Similarity	NPC471070
0.8815	High Similarity	NPC185066
0.8786	High Similarity	NPC14697
0.8768	High Similarity	NPC83535
0.8768	High Similarity	NPC31849
0.8759	High Similarity	NPC286038
0.875	High Similarity	NPC474289
0.8732	High Similarity	NPC287286
0.8731	High Similarity	NPC471827
0.8731	High Similarity	NPC471828
0.8723	High Similarity	NPC73078
0.8723	High Similarity	NPC148738
0.8723	High Similarity	NPC319870
0.8723	High Similarity	NPC327612
0.8714	High Similarity	NPC149320
0.8714	High Similarity	NPC476455
0.8714	High Similarity	NPC55615
0.8714	High Similarity	NPC128529
0.8714	High Similarity	NPC471630
0.8714	High Similarity	NPC283019
0.8714	High Similarity	NPC160727
0.8714	High Similarity	NPC283331
0.8714	High Similarity	NPC177281
0.8707	High Similarity	NPC103116
0.8699	High Similarity	NPC66991
0.8696	High Similarity	NPC175159
0.8686	High Similarity	NPC32463
0.8676	High Similarity	NPC472519
0.8676	High Similarity	NPC157212
0.8662	High Similarity	NPC312881
0.8657	High Similarity	NPC73413
0.8657	High Similarity	NPC201667
0.8657	High Similarity	NPC27671
0.8652	High Similarity	NPC155963
0.8643	High Similarity	NPC472424
0.8643	High Similarity	NPC471625
0.8643	High Similarity	NPC471909
0.8643	High Similarity	NPC86892
0.8643	High Similarity	NPC281241
0.863	High Similarity	NPC154217
0.863	High Similarity	NPC470322
0.8623	High Similarity	NPC66430
0.8623	High Similarity	NPC472517
0.8623	High Similarity	NPC37009
0.8621	High Similarity	NPC106126
0.8621	High Similarity	NPC108994
0.8621	High Similarity	NPC475719
0.8621	High Similarity	NPC101255
0.8621	High Similarity	NPC43716
0.8613	High Similarity	NPC168710
0.8603	High Similarity	NPC121740
0.8603	High Similarity	NPC258567
0.8603	High Similarity	NPC289316
0.8603	High Similarity	NPC243688
0.8603	High Similarity	NPC224774
0.8601	High Similarity	NPC152771
0.8601	High Similarity	NPC136095
0.8601	High Similarity	NPC195357
0.8592	High Similarity	NPC221046
0.8592	High Similarity	NPC279573
0.8592	High Similarity	NPC151946
0.8592	High Similarity	NPC211110
0.8582	High Similarity	NPC26954
0.8582	High Similarity	NPC315807
0.8582	High Similarity	NPC246177
0.8582	High Similarity	NPC38099
0.8582	High Similarity	NPC223616
0.8582	High Similarity	NPC472518
0.8582	High Similarity	NPC109675
0.8582	High Similarity	NPC317045
0.8582	High Similarity	NPC273772
0.8571	High Similarity	NPC47163
0.8571	High Similarity	NPC287182
0.8571	High Similarity	NPC84894
0.8571	High Similarity	NPC195343
0.8571	High Similarity	NPC224475
0.8571	High Similarity	NPC319859
0.8571	High Similarity	NPC166672
0.8571	High Similarity	NPC100986
0.8571	High Similarity	NPC62366
0.8571	High Similarity	NPC50896
0.8571	High Similarity	NPC213173
0.8571	High Similarity	NPC18804
0.8571	High Similarity	NPC198381
0.8571	High Similarity	NPC204353
0.8571	High Similarity	NPC180716
0.8571	High Similarity	NPC131950
0.8571	High Similarity	NPC267412
0.8571	High Similarity	NPC74655
0.8571	High Similarity	NPC260265
0.8571	High Similarity	NPC164269
0.8571	High Similarity	NPC326600
0.8571	High Similarity	NPC127888
0.8562	High Similarity	NPC196137
0.8562	High Similarity	NPC1886
0.8561	High Similarity	NPC194277
0.8561	High Similarity	NPC307289
0.8561	High Similarity	NPC19157
0.8551	High Similarity	NPC113098
0.854	High Similarity	NPC469453
0.8531	High Similarity	NPC36414
0.8529	High Similarity	NPC471826
0.8529	High Similarity	NPC101894
0.8529	High Similarity	NPC163248
0.8523	High Similarity	NPC474735
0.8521	High Similarity	NPC232246
0.8521	High Similarity	NPC153818
0.8521	High Similarity	NPC309452
0.8521	High Similarity	NPC472516
0.8511	High Similarity	NPC66705
0.8511	High Similarity	NPC472525
0.8507	High Similarity	NPC96286
0.8507	High Similarity	NPC248429
0.8503	High Similarity	NPC181388
0.85	High Similarity	NPC133956
0.85	High Similarity	NPC318400
0.85	High Similarity	NPC7526
0.85	High Similarity	NPC185777
0.85	High Similarity	NPC296624
0.85	High Similarity	NPC163557
0.85	High Similarity	NPC207002
0.85	High Similarity	NPC222036
0.85	High Similarity	NPC167111
0.85	High Similarity	NPC471910
0.8496	Intermediate Similarity	NPC235190
0.8496	Intermediate Similarity	NPC163200
0.8496	Intermediate Similarity	NPC180006
0.8493	Intermediate Similarity	NPC469701
0.8493	Intermediate Similarity	NPC470296
0.8493	Intermediate Similarity	NPC188632
0.8493	Intermediate Similarity	NPC87609
0.8493	Intermediate Similarity	NPC94794
0.8493	Intermediate Similarity	NPC112791
0.8493	Intermediate Similarity	NPC11700
0.8493	Intermediate Similarity	NPC196459
0.8489	Intermediate Similarity	NPC272650
0.8489	Intermediate Similarity	NPC267336
0.8489	Intermediate Similarity	NPC29734
0.8472	Intermediate Similarity	NPC472515
0.8472	Intermediate Similarity	NPC473209
0.8472	Intermediate Similarity	NPC254994
0.8467	Intermediate Similarity	NPC209142
0.8467	Intermediate Similarity	NPC290671
0.8467	Intermediate Similarity	NPC312549
0.8462	Intermediate Similarity	NPC23870
0.8462	Intermediate Similarity	NPC144512
0.8462	Intermediate Similarity	NPC47040
0.8462	Intermediate Similarity	NPC103001
0.8462	Intermediate Similarity	NPC137262
0.8462	Intermediate Similarity	NPC332594
0.8462	Intermediate Similarity	NPC37428
0.8462	Intermediate Similarity	NPC35501
0.8462	Intermediate Similarity	NPC278600
0.8462	Intermediate Similarity	NPC253616
0.8456	Intermediate Similarity	NPC19238
0.8456	Intermediate Similarity	NPC168259
0.8456	Intermediate Similarity	NPC244495
0.8456	Intermediate Similarity	NPC471114
0.8456	Intermediate Similarity	NPC93219
0.8451	Intermediate Similarity	NPC78746
0.8451	Intermediate Similarity	NPC104796
0.8451	Intermediate Similarity	NPC266245
0.8451	Intermediate Similarity	NPC188380
0.8451	Intermediate Similarity	NPC224543
0.8446	Intermediate Similarity	NPC10990
0.8446	Intermediate Similarity	NPC300988
0.844	Intermediate Similarity	NPC98179
0.844	Intermediate Similarity	NPC253574
0.844	Intermediate Similarity	NPC307412
0.844	Intermediate Similarity	NPC55149
0.8435	Intermediate Similarity	NPC206212
0.8435	Intermediate Similarity	NPC271288
0.8435	Intermediate Similarity	NPC469935
0.8435	Intermediate Similarity	NPC287275

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 NPC155552 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	915
0.2-0.3	1520
0.3-0.4	2462
0.4-0.5	2166
0.5-0.6	1149
0.6-0.7	433
0.7-0.8	141
0.8-0.85	34
0.85-0.9	15
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8686	High Similarity	NPD6859	Clinical (unspecified phase)
0.8671	High Similarity	NPD3750	Approved
0.8671	High Similarity	NPD6398	Clinical (unspecified phase)
0.8593	High Similarity	NPD2797	Approved
0.8582	High Similarity	NPD3748	Approved
0.8477	Intermediate Similarity	NPD7819	Suspended
0.8417	Intermediate Similarity	NPD3268	Approved
0.8369	Intermediate Similarity	NPD5124	Phase 1
0.8369	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8296	Intermediate Similarity	NPD422	Phase 1
0.8278	Intermediate Similarity	NPD6599	Discontinued
0.8264	Intermediate Similarity	NPD2796	Approved
0.8247	Intermediate Similarity	NPD7768	Phase 2
0.8235	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD7411	Suspended
0.8219	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD3267	Approved
0.8188	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD3266	Approved
0.8163	Intermediate Similarity	NPD4628	Phase 3
0.8156	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD1296	Phase 2
0.8151	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD4908	Phase 1
0.8138	Intermediate Similarity	NPD6100	Approved
0.8138	Intermediate Similarity	NPD6099	Approved
0.8121	Intermediate Similarity	NPD6799	Approved
0.8077	Intermediate Similarity	NPD7075	Discontinued
0.8069	Intermediate Similarity	NPD1510	Phase 2
0.8069	Intermediate Similarity	NPD2799	Discontinued
0.8052	Intermediate Similarity	NPD6801	Discontinued
0.8029	Intermediate Similarity	NPD1610	Phase 2
0.8027	Intermediate Similarity	NPD1549	Phase 2
0.8014	Intermediate Similarity	NPD1551	Phase 2
0.8013	Intermediate Similarity	NPD6273	Approved
0.7987	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD6355	Discontinued
0.7986	Intermediate Similarity	NPD3225	Approved
0.7963	Intermediate Similarity	NPD5844	Phase 1
0.7959	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD4308	Phase 3
0.7919	Intermediate Similarity	NPD7003	Approved
0.7902	Intermediate Similarity	NPD6798	Discontinued
0.7888	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD6832	Phase 2
0.7875	Intermediate Similarity	NPD7229	Phase 3
0.7868	Intermediate Similarity	NPD1548	Phase 1
0.7852	Intermediate Similarity	NPD1652	Phase 2
0.7852	Intermediate Similarity	NPD1243	Approved
0.7848	Intermediate Similarity	NPD3749	Approved
0.7847	Intermediate Similarity	NPD8032	Phase 2
0.7843	Intermediate Similarity	NPD5403	Approved
0.7843	Intermediate Similarity	NPD920	Approved
0.7842	Intermediate Similarity	NPD1608	Approved
0.7834	Intermediate Similarity	NPD3817	Phase 2
0.7834	Intermediate Similarity	NPD4288	Approved
0.7829	Intermediate Similarity	NPD5401	Approved
0.7823	Intermediate Similarity	NPD7033	Discontinued
0.7815	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD8127	Discontinued
0.7812	Intermediate Similarity	NPD7199	Phase 2
0.7806	Intermediate Similarity	NPD4380	Phase 2
0.78	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD4140	Approved
0.7793	Intermediate Similarity	NPD1240	Approved
0.7793	Intermediate Similarity	NPD4307	Phase 2
0.7785	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2313	Discontinued
0.7778	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD4476	Approved
0.777	Intermediate Similarity	NPD2935	Discontinued
0.777	Intermediate Similarity	NPD4477	Approved
0.7762	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD1778	Approved
0.7742	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD6002	Phase 3
0.7718	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD6004	Phase 3
0.7718	Intermediate Similarity	NPD6005	Phase 3
0.7718	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD9717	Approved
0.7712	Intermediate Similarity	NPD2533	Approved
0.7712	Intermediate Similarity	NPD2534	Approved
0.7712	Intermediate Similarity	NPD2532	Approved
0.7712	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD37	Approved
0.7687	Intermediate Similarity	NPD1607	Approved
0.7676	Intermediate Similarity	NPD1203	Approved
0.7673	Intermediate Similarity	NPD4965	Approved
0.7673	Intermediate Similarity	NPD4967	Phase 2
0.7673	Intermediate Similarity	NPD4966	Approved
0.7671	Intermediate Similarity	NPD4060	Phase 1
0.7628	Intermediate Similarity	NPD3226	Approved
0.7628	Intermediate Similarity	NPD7458	Discontinued
0.7626	Intermediate Similarity	NPD17	Approved
0.7622	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2798	Approved
0.7616	Intermediate Similarity	NPD2800	Approved
0.761	Intermediate Similarity	NPD5402	Approved
0.7609	Intermediate Similarity	NPD1894	Discontinued
0.7606	Intermediate Similarity	NPD1283	Approved
0.7603	Intermediate Similarity	NPD6233	Phase 2
0.76	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2346	Discontinued
0.7595	Intermediate Similarity	NPD1934	Approved
0.7586	Intermediate Similarity	NPD4625	Phase 3
0.7586	Intermediate Similarity	NPD7095	Approved
0.7578	Intermediate Similarity	NPD6234	Discontinued
0.7566	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD4110	Phase 3
0.7556	Intermediate Similarity	NPD5535	Approved
0.7554	Intermediate Similarity	NPD5585	Approved
0.7554	Intermediate Similarity	NPD5691	Approved
0.7547	Intermediate Similarity	NPD1465	Phase 2
0.7547	Intermediate Similarity	NPD2801	Approved
0.7546	Intermediate Similarity	NPD6232	Discontinued
0.7535	Intermediate Similarity	NPD4749	Approved
0.7534	Intermediate Similarity	NPD3764	Approved
0.7532	Intermediate Similarity	NPD1511	Approved
0.7531	Intermediate Similarity	NPD5494	Approved
0.7517	Intermediate Similarity	NPD2614	Approved
0.7516	Intermediate Similarity	NPD6971	Discontinued
0.7515	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD1241	Discontinued
0.75	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4626	Approved
0.7485	Intermediate Similarity	NPD6959	Discontinued
0.7483	Intermediate Similarity	NPD8651	Approved
0.7469	Intermediate Similarity	NPD919	Approved
0.7468	Intermediate Similarity	NPD6666	Approved
0.7468	Intermediate Similarity	NPD6667	Approved
0.7453	Intermediate Similarity	NPD3882	Suspended
0.7452	Intermediate Similarity	NPD1653	Approved
0.7451	Intermediate Similarity	NPD8166	Discontinued
0.745	Intermediate Similarity	NPD6651	Approved
0.7447	Intermediate Similarity	NPD3496	Discontinued
0.744	Intermediate Similarity	NPD5953	Discontinued
0.7438	Intermediate Similarity	NPD8455	Phase 2
0.7436	Intermediate Similarity	NPD1512	Approved
0.7434	Intermediate Similarity	NPD4534	Discontinued
0.7432	Intermediate Similarity	NPD2979	Phase 3
0.7425	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7097	Phase 1
0.7396	Intermediate Similarity	NPD6559	Discontinued
0.7394	Intermediate Similarity	NPD1281	Approved
0.7389	Intermediate Similarity	NPD7427	Discontinued
0.7389	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1019	Discontinued
0.7368	Intermediate Similarity	NPD5762	Approved
0.7368	Intermediate Similarity	NPD5763	Approved
0.7368	Intermediate Similarity	NPD3134	Approved
0.7365	Intermediate Similarity	NPD4062	Phase 3
0.7365	Intermediate Similarity	NPD3818	Discontinued
0.7357	Intermediate Similarity	NPD9545	Approved
0.7353	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD3972	Approved
0.7329	Intermediate Similarity	NPD2861	Phase 2
0.7325	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD3847	Discontinued
0.7321	Intermediate Similarity	NPD7286	Phase 2
0.7315	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1613	Approved
0.7308	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2438	Suspended
0.7297	Intermediate Similarity	NPD411	Approved
0.7293	Intermediate Similarity	NPD9697	Approved
0.7292	Intermediate Similarity	NPD4359	Approved
0.7279	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1535	Discovery
0.7267	Intermediate Similarity	NPD4622	Approved
0.7267	Intermediate Similarity	NPD447	Suspended
0.7267	Intermediate Similarity	NPD4340	Discontinued
0.7267	Intermediate Similarity	NPD1933	Approved
0.7267	Intermediate Similarity	NPD230	Phase 1
0.7267	Intermediate Similarity	NPD4618	Approved
0.7266	Intermediate Similarity	NPD7157	Approved
0.7262	Intermediate Similarity	NPD7228	Approved
0.7251	Intermediate Similarity	NPD7549	Discontinued
0.725	Intermediate Similarity	NPD6502	Phase 2
0.7248	Intermediate Similarity	NPD6663	Approved
0.7246	Intermediate Similarity	NPD6166	Phase 2
0.7246	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1876	Approved
0.7235	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7315	Approved
0.7222	Intermediate Similarity	NPD1481	Phase 2
0.7219	Intermediate Similarity	NPD7054	Approved
0.7212	Intermediate Similarity	NPD6746	Phase 2

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