NPASS Compound

Structure

NPC469891 OpenBabel07101719252D 28 30 0 0 1 0 0 0 0 0999 V2000 1.8660 2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 2.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 -0.7601 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 1.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8660 2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3660 3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3660 3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8660 2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 0.5000 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 2.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8660 2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 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 0.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 25 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 21 2 0 0 0 0 11 21 1 0 0 0 0 12 13 2 0 0 0 0 12 17 1 0 0 0 0 13 21 1 0 0 0 0 14 18 1 0 0 0 0 14 19 2 0 0 0 0 15 17 2 0 0 0 0 15 25 1 0 0 0 0 16 20 2 0 0 0 0 16 25 1 0 0 0 0 18 2 1 1 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 22 20 1 6 0 0 0 22 23 1 0 0 0 0 23 26 1 1 0 0 0 24 26 1 0 0 0 0 24 27 2 0 0 0 0 24 28 1 0 0 0 0 25 26 1 6 0 0 0 26 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.24
Volume:	429.071
LogP:	5.979
LogD:	4.388
LogS:	-4.517
# Rotatable Bonds:	4
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.479
Synthetic Accessibility Score:	4.531
Fsp3:	0.423
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:	-4.836
MDCK Permeability:	3.301346077932976e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.071
Plasma Protein Binding (PPB):	96.96929168701172%
Volume Distribution (VD):	0.69
Pgp-substrate:	3.3073267936706543%

ADMET: Metabolism

CYP1A2-inhibitor:	0.55
CYP1A2-substrate:	0.513
CYP2C19-inhibitor:	0.15
CYP2C19-substrate:	0.744
CYP2C9-inhibitor:	0.801
CYP2C9-substrate:	0.863
CYP2D6-inhibitor:	0.351
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.872
CYP3A4-substrate:	0.45

ADMET: Excretion

Clearance (CL):	1.389
Half-life (T1/2):	0.179

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.285
Drug-inuced Liver Injury (DILI):	0.425
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.104
Maximum Recommended Daily Dose:	0.138
Skin Sensitization:	0.877
Carcinogencity:	0.45
Eye Corrosion:	0.057
Eye Irritation:	0.551
Respiratory Toxicity:	0.52

Download Data

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

Natural Product: NPC469891

Natural Product ID:	NPC469891
*Common Name:**	27-Nor-Zyggomphic Acid B
IUPAC Name:	(1R,3aR,4R,5S,7aS)-1,3,4,5,7-pentamethyl-5-[(1E,3E)-2-methyl-4-phenylbuta-1,3-dienyl]-3a,7a-dihydro-1H-indene-4-carboxylic acid
Synonyms:
Standard InCHIKey:	USZQRGFOPCNWMR-UQCZAKNZSA-N
Standard InCHI:	InChI=1S/C26H32O2/c1-17(12-13-21-10-8-7-9-11-21)15-25(5)16-20(4)22-18(2)14-19(3)23(22)26(25,6)24(27)28/h7-16,18,22-23H,1-6H3,(H,27,28)/b13-12+,17-15+/t18-,22-,23+,25+,26+/m1/s1
SMILES:	CC1C=C(C2C1C(=CC(C2(C)C(=O)O)(C)C=C(C)C=CC3=CC=CC=C3)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224900
PubChem CID:	46938443
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO22559	Plakortis halichondrioides	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11277739]
NPO22559	Plakortis halichondrioides	Species	Plakinidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[12762801]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14703354]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1800643]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	Brazil	n.a.	PMID[18177008]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	caribbean	n.a.	PMID[20738102]
NPO22559	Plakortis halichondrioides	Species	Plakinidae	Eukaryota	n.a.	caribbean	n.a.	PMID[20738102]
NPO22559	Plakortis halichondrioides	Species	Plakinidae	Eukaryota	n.a.	Puerto Rican	n.a.	PMID[20923180]
NPO22559	Plakortis halichondrioides	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277322]
NPO22559	Plakortis halichondrioides	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882424]
NPO23250	Plakortis angulospiculatus	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22559	Plakortis halichondrioides	Species	Plakinidae	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
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	2280.0	nM	PMID[488173]
NPT2	Others	Unspecified		IC50	=	18600.0	nM	PMID[488173]

☑ 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 NPC469891 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	166
0.1-0.2	907
0.2-0.3	2501
0.3-0.4	9987
0.4-0.5	20177
0.5-0.6	7568
0.6-0.7	1235
0.7-0.8	136
0.8-0.85	11
0.85-0.9	3
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469892
1.0	High Similarity	NPC469890
0.989	High Similarity	NPC120393
0.9889	High Similarity	NPC469893
0.9677	High Similarity	NPC264728
0.899	High Similarity	NPC244933
0.899	High Similarity	NPC85560
0.8485	Intermediate Similarity	NPC136810
0.8485	Intermediate Similarity	NPC133809
0.8485	Intermediate Similarity	NPC128248
0.8485	Intermediate Similarity	NPC225079
0.8367	Intermediate Similarity	NPC251579
0.8367	Intermediate Similarity	NPC133135
0.8182	Intermediate Similarity	NPC226041
0.8144	Intermediate Similarity	NPC475057
0.8077	Intermediate Similarity	NPC142326
0.8077	Intermediate Similarity	NPC94751
0.8073	Intermediate Similarity	NPC9274
0.8041	Intermediate Similarity	NPC475023
0.8041	Intermediate Similarity	NPC86987
0.8041	Intermediate Similarity	NPC475059
0.802	Intermediate Similarity	NPC221825
0.802	Intermediate Similarity	NPC7435
0.7957	Intermediate Similarity	NPC44830
0.7938	Intermediate Similarity	NPC70940
0.7938	Intermediate Similarity	NPC274455
0.7938	Intermediate Similarity	NPC86670
0.789	Intermediate Similarity	NPC294458
0.7885	Intermediate Similarity	NPC329282
0.783	Intermediate Similarity	NPC21929
0.7812	Intermediate Similarity	NPC322387
0.7798	Intermediate Similarity	NPC206414
0.7798	Intermediate Similarity	NPC477476
0.7798	Intermediate Similarity	NPC287055
0.7798	Intermediate Similarity	NPC477475
0.7798	Intermediate Similarity	NPC242957
0.7798	Intermediate Similarity	NPC306977
0.7778	Intermediate Similarity	NPC475002
0.7778	Intermediate Similarity	NPC95126
0.7736	Intermediate Similarity	NPC37914
0.7732	Intermediate Similarity	NPC329064
0.7723	Intermediate Similarity	NPC261947
0.7684	Intermediate Similarity	NPC267704
0.7647	Intermediate Similarity	NPC477767
0.7642	Intermediate Similarity	NPC471186
0.7636	Intermediate Similarity	NPC93287
0.7634	Intermediate Similarity	NPC127343
0.7624	Intermediate Similarity	NPC172925
0.7619	Intermediate Similarity	NPC247976
0.7576	Intermediate Similarity	NPC84288
0.7573	Intermediate Similarity	NPC271475
0.7545	Intermediate Similarity	NPC218855
0.7524	Intermediate Similarity	NPC475978
0.7524	Intermediate Similarity	NPC474820
0.75	Intermediate Similarity	NPC221275
0.75	Intermediate Similarity	NPC249811
0.7456	Intermediate Similarity	NPC45794
0.7453	Intermediate Similarity	NPC329556
0.7431	Intermediate Similarity	NPC475006
0.7429	Intermediate Similarity	NPC94487
0.7411	Intermediate Similarity	NPC234637
0.7411	Intermediate Similarity	NPC130591
0.7411	Intermediate Similarity	NPC471721
0.7407	Intermediate Similarity	NPC100767
0.7396	Intermediate Similarity	NPC285773
0.7391	Intermediate Similarity	NPC472698
0.7391	Intermediate Similarity	NPC472697
0.7368	Intermediate Similarity	NPC212891
0.7339	Intermediate Similarity	NPC112903
0.7333	Intermediate Similarity	NPC54647
0.7328	Intermediate Similarity	NPC202015
0.7327	Intermediate Similarity	NPC220596
0.7321	Intermediate Similarity	NPC469547
0.7321	Intermediate Similarity	NPC470253
0.7321	Intermediate Similarity	NPC471481
0.73	Intermediate Similarity	NPC298115
0.7297	Intermediate Similarity	NPC265513
0.7265	Intermediate Similarity	NPC470585
0.7255	Intermediate Similarity	NPC1682
0.7255	Intermediate Similarity	NPC188844
0.7248	Intermediate Similarity	NPC185763
0.7248	Intermediate Similarity	NPC83409
0.7248	Intermediate Similarity	NPC191215
0.7248	Intermediate Similarity	NPC274089
0.7245	Intermediate Similarity	NPC95965
0.7238	Intermediate Similarity	NPC179411
0.7232	Intermediate Similarity	NPC471188
0.7232	Intermediate Similarity	NPC280789
0.7232	Intermediate Similarity	NPC66208
0.7232	Intermediate Similarity	NPC471189
0.7228	Intermediate Similarity	NPC26224
0.7222	Intermediate Similarity	NPC19136
0.7222	Intermediate Similarity	NPC472222
0.7222	Intermediate Similarity	NPC56168
0.7222	Intermediate Similarity	NPC472221
0.7217	Intermediate Similarity	NPC242764
0.7217	Intermediate Similarity	NPC105141
0.7216	Intermediate Similarity	NPC477770
0.72	Intermediate Similarity	NPC477693
0.72	Intermediate Similarity	NPC477704
0.7196	Intermediate Similarity	NPC304873
0.7193	Intermediate Similarity	NPC217111
0.719	Intermediate Similarity	NPC470816
0.7179	Intermediate Similarity	NPC79933
0.7179	Intermediate Similarity	NPC473974
0.7179	Intermediate Similarity	NPC31296
0.7179	Intermediate Similarity	NPC258366
0.7179	Intermediate Similarity	NPC42657
0.7172	Intermediate Similarity	NPC243166
0.7168	Intermediate Similarity	NPC143768
0.7167	Intermediate Similarity	NPC328107
0.7167	Intermediate Similarity	NPC473938
0.7157	Intermediate Similarity	NPC284475
0.7157	Intermediate Similarity	NPC125226
0.7155	Intermediate Similarity	NPC471926
0.7143	Intermediate Similarity	NPC155429
0.7143	Intermediate Similarity	NPC239185
0.7119	Intermediate Similarity	NPC234337
0.7119	Intermediate Similarity	NPC183339
0.7119	Intermediate Similarity	NPC133389
0.7113	Intermediate Similarity	NPC230068
0.7103	Intermediate Similarity	NPC469481
0.7097	Intermediate Similarity	NPC475138
0.7094	Intermediate Similarity	NPC254233
0.7091	Intermediate Similarity	NPC472700
0.7091	Intermediate Similarity	NPC472699
0.7087	Intermediate Similarity	NPC59677
0.7087	Intermediate Similarity	NPC471864
0.7087	Intermediate Similarity	NPC153885
0.7087	Intermediate Similarity	NPC314690
0.708	Intermediate Similarity	NPC292834
0.7075	Intermediate Similarity	NPC75724
0.7075	Intermediate Similarity	NPC317280
0.7075	Intermediate Similarity	NPC134882
0.7075	Intermediate Similarity	NPC329387
0.7069	Intermediate Similarity	NPC471928
0.7069	Intermediate Similarity	NPC471925
0.7069	Intermediate Similarity	NPC471924
0.7059	Intermediate Similarity	NPC241001
0.7053	Intermediate Similarity	NPC103488
0.7049	Intermediate Similarity	NPC100402
0.7049	Intermediate Similarity	NPC9180
0.7043	Intermediate Similarity	NPC186933
0.7043	Intermediate Similarity	NPC476357
0.7043	Intermediate Similarity	NPC215419
0.7043	Intermediate Similarity	NPC93181
0.7041	Intermediate Similarity	NPC270507
0.7041	Intermediate Similarity	NPC83569
0.7041	Intermediate Similarity	NPC288903
0.7041	Intermediate Similarity	NPC69279
0.7037	Intermediate Similarity	NPC474112
0.7034	Intermediate Similarity	NPC204784
0.7027	Intermediate Similarity	NPC472696
0.7027	Intermediate Similarity	NPC472683
0.7027	Intermediate Similarity	NPC472701
0.7027	Intermediate Similarity	NPC472695
0.7025	Intermediate Similarity	NPC12881
0.7025	Intermediate Similarity	NPC140118
0.7019	Intermediate Similarity	NPC238219
0.7009	Intermediate Similarity	NPC152812
0.7009	Intermediate Similarity	NPC217621
0.7008	Intermediate Similarity	NPC203486
0.7	Intermediate Similarity	NPC321670
0.7	Intermediate Similarity	NPC269923
0.7	Intermediate Similarity	NPC105899
0.7	Intermediate Similarity	NPC369
0.7	Intermediate Similarity	NPC293831
0.7	Intermediate Similarity	NPC167323
0.6992	Remote Similarity	NPC171007
0.6992	Remote Similarity	NPC190849
0.6991	Remote Similarity	NPC474057
0.699	Remote Similarity	NPC187725
0.699	Remote Similarity	NPC79917
0.699	Remote Similarity	NPC133461
0.699	Remote Similarity	NPC141607
0.6981	Remote Similarity	NPC265220
0.6981	Remote Similarity	NPC253423
0.6981	Remote Similarity	NPC240042
0.6981	Remote Similarity	NPC324602
0.6979	Remote Similarity	NPC274996
0.6979	Remote Similarity	NPC196827
0.6979	Remote Similarity	NPC477371
0.6975	Remote Similarity	NPC318552
0.6975	Remote Similarity	NPC474223
0.6975	Remote Similarity	NPC190501
0.6975	Remote Similarity	NPC475804
0.6975	Remote Similarity	NPC475827
0.6975	Remote Similarity	NPC474222
0.6972	Remote Similarity	NPC274443
0.6972	Remote Similarity	NPC255676
0.6964	Remote Similarity	NPC318327
0.6961	Remote Similarity	NPC9822
0.6952	Remote Similarity	NPC260233
0.6944	Remote Similarity	NPC289117
0.6944	Remote Similarity	NPC109514
0.6944	Remote Similarity	NPC476993
0.6942	Remote Similarity	NPC121168
0.6939	Remote Similarity	NPC323103
0.6939	Remote Similarity	NPC103387
0.6937	Remote Similarity	NPC329705

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 NPC469891 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	789
0.2-0.3	1477
0.3-0.4	3097
0.4-0.5	2407
0.5-0.6	965
0.6-0.7	202
0.7-0.8	46
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8144	Intermediate Similarity	NPD1088	Approved
0.8061	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.8021	Intermediate Similarity	NPD5347	Phase 2
0.8021	Intermediate Similarity	NPD5346	Phase 2
0.7938	Intermediate Similarity	NPD1089	Approved
0.7938	Intermediate Similarity	NPD1086	Approved
0.7938	Intermediate Similarity	NPD1090	Approved
0.7835	Intermediate Similarity	NPD800	Approved
0.7812	Intermediate Similarity	NPD4793	Discontinued
0.78	Intermediate Similarity	NPD1693	Approved
0.7798	Intermediate Similarity	NPD6858	Approved
0.7798	Intermediate Similarity	NPD7094	Approved
0.7742	Intermediate Similarity	NPD226	Approved
0.767	Intermediate Similarity	NPD2066	Phase 3
0.7629	Intermediate Similarity	NPD1087	Approved
0.7624	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1239	Approved
0.7476	Intermediate Similarity	NPD1565	Approved
0.7476	Intermediate Similarity	NPD1564	Approved
0.7476	Intermediate Similarity	NPD1566	Phase 3
0.7456	Intermediate Similarity	NPD7610	Discontinued
0.7453	Intermediate Similarity	NPD1930	Approved
0.7453	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5765	Approved
0.7453	Intermediate Similarity	NPD1929	Approved
0.7451	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6049	Phase 2
0.7423	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD225	Approved
0.7419	Intermediate Similarity	NPD227	Approved
0.7407	Intermediate Similarity	NPD6685	Approved
0.74	Intermediate Similarity	NPD3672	Approved
0.74	Intermediate Similarity	NPD3673	Approved
0.7396	Intermediate Similarity	NPD9491	Approved
0.7391	Intermediate Similarity	NPD7009	Phase 2
0.7345	Intermediate Similarity	NPD5951	Approved
0.729	Intermediate Similarity	NPD6647	Phase 2
0.7257	Intermediate Similarity	NPD6010	Discontinued
0.7255	Intermediate Similarity	NPD7631	Approved
0.7212	Intermediate Similarity	NPD1989	Approved
0.7196	Intermediate Similarity	NPD1932	Approved
0.7193	Intermediate Similarity	NPD4766	Approved
0.7184	Intermediate Similarity	NPD1563	Approved
0.7157	Intermediate Similarity	NPD7609	Phase 3
0.7143	Intermediate Similarity	NPD3495	Discontinued
0.7143	Intermediate Similarity	NPD3643	Approved
0.7143	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3642	Approved
0.7143	Intermediate Similarity	NPD3644	Approved
0.713	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD2932	Approved
0.7119	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2329	Discontinued
0.7069	Intermediate Similarity	NPD3797	Approved
0.7064	Intermediate Similarity	NPD5909	Discontinued
0.7048	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD2629	Approved
0.7041	Intermediate Similarity	NPD3971	Phase 1
0.7	Intermediate Similarity	NPD5618	Discontinued
0.6984	Remote Similarity	NPD7961	Discontinued
0.6979	Remote Similarity	NPD9490	Approved
0.6975	Remote Similarity	NPD3019	Approved
0.6975	Remote Similarity	NPD4199	Phase 3
0.6949	Remote Similarity	NPD3798	Phase 3
0.6949	Remote Similarity	NPD4479	Discontinued
0.6935	Remote Similarity	NPD5736	Approved
0.693	Remote Similarity	NPD6912	Phase 3
0.6917	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD253	Approved
0.6903	Remote Similarity	NPD5278	Discontinued
0.6852	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6663	Approved
0.6847	Remote Similarity	NPD5048	Discontinued
0.681	Remote Similarity	NPD3598	Phase 3
0.6765	Remote Similarity	NPD650	Approved
0.6754	Remote Similarity	NPD1317	Discontinued
0.6723	Remote Similarity	NPD6065	Approved
0.6698	Remote Similarity	NPD1066	Discontinued
0.6697	Remote Similarity	NPD7798	Approved
0.6696	Remote Similarity	NPD1018	Approved
0.6667	Remote Similarity	NPD2650	Approved
0.6667	Remote Similarity	NPD2652	Approved
0.6667	Remote Similarity	NPD7084	Phase 3
0.6641	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD3023	Approved
0.6639	Remote Similarity	NPD3026	Approved
0.6612	Remote Similarity	NPD3025	Approved
0.6612	Remote Similarity	NPD3024	Approved
0.6609	Remote Similarity	NPD4234	Approved
0.6609	Remote Similarity	NPD4233	Approved
0.6604	Remote Similarity	NPD1508	Approved
0.6591	Remote Similarity	NPD7305	Phase 1
0.6581	Remote Similarity	NPD2607	Approved
0.6571	Remote Similarity	NPD9256	Approved
0.6571	Remote Similarity	NPD9258	Approved
0.6562	Remote Similarity	NPD9716	Approved
0.6562	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD4198	Discontinued
0.6552	Remote Similarity	NPD5927	Discontinued
0.6538	Remote Similarity	NPD1101	Approved
0.6525	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD9566	Approved
0.6509	Remote Similarity	NPD5284	Approved
0.6509	Remote Similarity	NPD5281	Approved
0.6496	Remote Similarity	NPD7236	Approved
0.6484	Remote Similarity	NPD7055	Discontinued
0.6481	Remote Similarity	NPD4814	Discontinued
0.6475	Remote Similarity	NPD5981	Approved
0.6466	Remote Similarity	NPD1756	Approved
0.6466	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD1752	Approved
0.6462	Remote Similarity	NPD8032	Phase 2
0.6457	Remote Similarity	NPD6085	Phase 2
0.6457	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5926	Approved
0.6455	Remote Similarity	NPD9495	Approved
0.6434	Remote Similarity	NPD7008	Discontinued
0.6423	Remote Similarity	NPD2345	Approved
0.6423	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD1843	Approved
0.641	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD1067	Discontinued
0.6393	Remote Similarity	NPD7741	Discontinued
0.6389	Remote Similarity	NPD3718	Approved
0.6389	Remote Similarity	NPD1202	Approved
0.6389	Remote Similarity	NPD720	Approved
0.6389	Remote Similarity	NPD719	Approved
0.6389	Remote Similarity	NPD3719	Approved
0.6387	Remote Similarity	NPD7077	Approved
0.6387	Remote Similarity	NPD7076	Approved
0.6372	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5162	Approved
0.6348	Remote Similarity	NPD467	Phase 1
0.6346	Remote Similarity	NPD9259	Approved
0.6346	Remote Similarity	NPD9257	Approved
0.6341	Remote Similarity	NPD6993	Approved
0.6341	Remote Similarity	NPD6994	Approved
0.6341	Remote Similarity	NPD1855	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD7714	Approved
0.6336	Remote Similarity	NPD7715	Approved
0.633	Remote Similarity	NPD4094	Approved
0.632	Remote Similarity	NPD2612	Approved
0.632	Remote Similarity	NPD3132	Approved
0.632	Remote Similarity	NPD2609	Approved
0.632	Remote Similarity	NPD2608	Approved
0.632	Remote Similarity	NPD3131	Approved
0.632	Remote Similarity	NPD4807	Approved
0.632	Remote Similarity	NPD2611	Approved
0.632	Remote Similarity	NPD4218	Approved
0.632	Remote Similarity	NPD4217	Approved
0.632	Remote Similarity	NPD4216	Approved
0.632	Remote Similarity	NPD4806	Approved
0.632	Remote Similarity	NPD2610	Approved
0.632	Remote Similarity	NPD4215	Approved
0.6299	Remote Similarity	NPD1283	Approved
0.6296	Remote Similarity	NPD752	Approved
0.629	Remote Similarity	NPD5305	Approved
0.629	Remote Similarity	NPD5306	Approved
0.629	Remote Similarity	NPD4059	Approved
0.6281	Remote Similarity	NPD3317	Approved
0.6277	Remote Similarity	NPD7082	Approved
0.6271	Remote Similarity	NPD188	Approved
0.6271	Remote Similarity	NPD189	Phase 3
0.627	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD7239	Suspended
0.626	Remote Similarity	NPD3091	Approved
0.626	Remote Similarity	NPD2617	Discontinued
0.625	Remote Similarity	NPD3020	Approved
0.625	Remote Similarity	NPD6563	Approved
0.625	Remote Similarity	NPD6565	Approved
0.625	Remote Similarity	NPD6564	Approved
0.624	Remote Similarity	NPD3881	Discontinued
0.624	Remote Similarity	NPD4879	Approved
0.624	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD1409	Phase 3
0.6239	Remote Similarity	NPD2182	Approved
0.6238	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD8166	Discontinued
0.6232	Remote Similarity	NPD7259	Approved
0.6216	Remote Similarity	NPD1875	Phase 1
0.6216	Remote Similarity	NPD4655	Approved
0.6216	Remote Similarity	NPD4657	Approved
0.621	Remote Similarity	NPD1245	Approved
0.621	Remote Similarity	NPD4102	Approved
0.621	Remote Similarity	NPD4105	Approved
0.621	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.621	Remote Similarity	NPD4163	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5704	Approved
0.6207	Remote Similarity	NPD5705	Approved
0.6207	Remote Similarity	NPD5706	Approved
0.6202	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD1246	Approved
0.6195	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5280	Approved
0.619	Remote Similarity	NPD4694	Approved
0.6187	Remote Similarity	NPD7295	Approved
0.6186	Remote Similarity	NPD2067	Discontinued
0.6182	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD2115	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