NPASS Compound

Structure

NPC469893 OpenBabel07101719252D 27 29 0 0 1 0 0 0 0 0999 V2000 -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 1.3660 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 3.3660 1.3660 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 5.3660 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 3.8660 2.2321 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 -2.4049 1.0000 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 -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 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 24 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 10 1 0 0 0 0 9 13 2 0 0 0 0 10 14 2 0 0 0 0 11 20 2 0 0 0 0 12 20 1 0 0 0 0 13 20 1 0 0 0 0 14 24 1 0 0 0 0 15 17 1 0 0 0 0 15 18 2 0 0 0 0 16 19 2 0 0 0 0 16 24 1 0 0 0 0 17 1 1 1 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 21 19 1 6 0 0 0 21 22 1 0 0 0 0 22 25 1 1 0 0 0 23 25 1 0 0 0 0 23 26 2 0 0 0 0 23 27 1 0 0 0 0 24 25 1 6 0 0 0 25 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.22
Volume:	411.775
LogP:	5.864
LogD:	4.304
LogS:	-3.942
# 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:	0.516
Synthetic Accessibility Score:	4.544
Fsp3:	0.4
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:	-4.802
MDCK Permeability:	2.7071913791587576e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.246
Plasma Protein Binding (PPB):	93.11993408203125%
Volume Distribution (VD):	0.849
Pgp-substrate:	5.104592323303223%

ADMET: Metabolism

CYP1A2-inhibitor:	0.553
CYP1A2-substrate:	0.412
CYP2C19-inhibitor:	0.126
CYP2C19-substrate:	0.761
CYP2C9-inhibitor:	0.743
CYP2C9-substrate:	0.893
CYP2D6-inhibitor:	0.452
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.88
CYP3A4-substrate:	0.409

ADMET: Excretion

Clearance (CL):	1.062
Half-life (T1/2):	0.103

ADMET: Toxicity

hERG Blockers:	0.134
Human Hepatotoxicity (H-HT):	0.207
Drug-inuced Liver Injury (DILI):	0.803
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.053
Maximum Recommended Daily Dose:	0.198
Skin Sensitization:	0.81
Carcinogencity:	0.533
Eye Corrosion:	0.34
Eye Irritation:	0.786
Respiratory Toxicity:	0.709

Download Data

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

Natural Product: NPC469893

Natural Product ID:	NPC469893
*Common Name:**	22,27-Dinor-Zyggomphic Acid B
IUPAC Name:	(1R,3aR,4R,5S,7aS)-1,3,4,5,7-pentamethyl-5-[(1E,3E)-4-phenylbuta-1,3-dienyl]-3a,7a-dihydro-1H-indene-4-carboxylic acid
Synonyms:
Standard InCHIKey:	KNDMYWMVTUEPLZ-MACPZBPUSA-N
Standard InCHI:	InChI=1S/C25H30O2/c1-17-15-18(2)22-21(17)19(3)16-24(4,25(22,5)23(26)27)14-10-9-13-20-11-7-6-8-12-20/h6-17,21-22H,1-5H3,(H,26,27)/b13-9+,14-10+/t17-,21-,22+,24+,25+/m1/s1
SMILES:	CC1=C[C@H]([C@H]2[C@H]1[C@@](C)(C(=O)O)[C@@](C=C2C)(C)/C=C/C=C/c1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224902
PubChem CID:	46938548
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000037] Styrenes

*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]
NPO22559	Plakortis halichondrioides	Species	Plakinidae	Eukaryota	n.a.	caribbean	n.a.	PMID[20738102]
NPO23250	Plakortis angulospiculatus	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]
NPO22559	Plakortis halichondrioides	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23250	Plakortis angulospiculatus	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	=	27900.0	nM	PMID[529982]
NPT2	Others	Unspecified		IC50	=	30400.0	nM	PMID[529982]

☑ 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 NPC469893 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
0.9889	High Similarity	NPC469892
0.9889	High Similarity	NPC469891
0.9889	High Similarity	NPC469890
0.978	High Similarity	NPC120393
0.957	High Similarity	NPC264728
0.8889	High Similarity	NPC85560
0.8889	High Similarity	NPC244933
0.8571	High Similarity	NPC133809
0.8571	High Similarity	NPC225079
0.8571	High Similarity	NPC136810
0.8571	High Similarity	NPC128248
0.8265	Intermediate Similarity	NPC133135
0.8265	Intermediate Similarity	NPC226041
0.8265	Intermediate Similarity	NPC251579
0.8155	Intermediate Similarity	NPC94751
0.8155	Intermediate Similarity	NPC142326
0.8125	Intermediate Similarity	NPC475059
0.8125	Intermediate Similarity	NPC475023
0.8125	Intermediate Similarity	NPC86987
0.81	Intermediate Similarity	NPC221825
0.8043	Intermediate Similarity	NPC44830
0.8041	Intermediate Similarity	NPC475057
0.8021	Intermediate Similarity	NPC70940
0.8021	Intermediate Similarity	NPC274455
0.8021	Intermediate Similarity	NPC86670
0.7982	Intermediate Similarity	NPC9274
0.7961	Intermediate Similarity	NPC329282
0.7921	Intermediate Similarity	NPC7435
0.7895	Intermediate Similarity	NPC322387
0.787	Intermediate Similarity	NPC287055
0.787	Intermediate Similarity	NPC206414
0.787	Intermediate Similarity	NPC242957
0.787	Intermediate Similarity	NPC306977
0.785	Intermediate Similarity	NPC95126
0.785	Intermediate Similarity	NPC475002
0.7812	Intermediate Similarity	NPC329064
0.781	Intermediate Similarity	NPC37914
0.78	Intermediate Similarity	NPC261947
0.7798	Intermediate Similarity	NPC294458
0.7766	Intermediate Similarity	NPC267704
0.7736	Intermediate Similarity	NPC21929
0.7717	Intermediate Similarity	NPC127343
0.7714	Intermediate Similarity	NPC471186
0.7706	Intermediate Similarity	NPC477475
0.7706	Intermediate Similarity	NPC477476
0.7706	Intermediate Similarity	NPC93287
0.77	Intermediate Similarity	NPC172925
0.7692	Intermediate Similarity	NPC247976
0.757	Intermediate Similarity	NPC249811
0.7568	Intermediate Similarity	NPC221275
0.7549	Intermediate Similarity	NPC477767
0.7524	Intermediate Similarity	NPC329556
0.75	Intermediate Similarity	NPC475006
0.7477	Intermediate Similarity	NPC471721
0.7477	Intermediate Similarity	NPC100767
0.7476	Intermediate Similarity	NPC271475
0.7475	Intermediate Similarity	NPC84288
0.7474	Intermediate Similarity	NPC285773
0.7455	Intermediate Similarity	NPC218855
0.7434	Intermediate Similarity	NPC212891
0.7429	Intermediate Similarity	NPC475978
0.7429	Intermediate Similarity	NPC474820
0.7407	Intermediate Similarity	NPC112903
0.7404	Intermediate Similarity	NPC54647
0.74	Intermediate Similarity	NPC220596
0.7387	Intermediate Similarity	NPC470253
0.7374	Intermediate Similarity	NPC298115
0.7368	Intermediate Similarity	NPC45794
0.7364	Intermediate Similarity	NPC265513
0.7333	Intermediate Similarity	NPC94487
0.7328	Intermediate Similarity	NPC470585
0.7321	Intermediate Similarity	NPC234637
0.7321	Intermediate Similarity	NPC130591
0.732	Intermediate Similarity	NPC95965
0.7315	Intermediate Similarity	NPC185763
0.7315	Intermediate Similarity	NPC83409
0.7308	Intermediate Similarity	NPC179411
0.7304	Intermediate Similarity	NPC472697
0.7304	Intermediate Similarity	NPC472698
0.73	Intermediate Similarity	NPC26224
0.7297	Intermediate Similarity	NPC471189
0.7297	Intermediate Similarity	NPC471188
0.7297	Intermediate Similarity	NPC66208
0.7297	Intermediate Similarity	NPC280789
0.729	Intermediate Similarity	NPC472221
0.729	Intermediate Similarity	NPC472222
0.7273	Intermediate Similarity	NPC477693
0.7273	Intermediate Similarity	NPC477704
0.7264	Intermediate Similarity	NPC304873
0.7245	Intermediate Similarity	NPC243166
0.7241	Intermediate Similarity	NPC202015
0.7241	Intermediate Similarity	NPC42657
0.7232	Intermediate Similarity	NPC469547
0.7232	Intermediate Similarity	NPC143768
0.7232	Intermediate Similarity	NPC471481
0.7228	Intermediate Similarity	NPC125226
0.7222	Intermediate Similarity	NPC155429
0.7212	Intermediate Similarity	NPC239185
0.7188	Intermediate Similarity	NPC230068
0.7179	Intermediate Similarity	NPC183339
0.7179	Intermediate Similarity	NPC133389
0.7179	Intermediate Similarity	NPC234337
0.717	Intermediate Similarity	NPC469481
0.7157	Intermediate Similarity	NPC153885
0.7157	Intermediate Similarity	NPC1682
0.7157	Intermediate Similarity	NPC188844
0.7157	Intermediate Similarity	NPC314690
0.7157	Intermediate Similarity	NPC59677
0.7156	Intermediate Similarity	NPC274089
0.7156	Intermediate Similarity	NPC191215
0.7143	Intermediate Similarity	NPC75724
0.7143	Intermediate Similarity	NPC134882
0.7143	Intermediate Similarity	NPC329387
0.7143	Intermediate Similarity	NPC292834
0.7143	Intermediate Similarity	NPC317280
0.713	Intermediate Similarity	NPC105141
0.713	Intermediate Similarity	NPC242764
0.713	Intermediate Similarity	NPC19136
0.713	Intermediate Similarity	NPC471925
0.713	Intermediate Similarity	NPC56168
0.713	Intermediate Similarity	NPC471924
0.713	Intermediate Similarity	NPC471928
0.7128	Intermediate Similarity	NPC103488
0.7119	Intermediate Similarity	NPC241001
0.7113	Intermediate Similarity	NPC477770
0.7113	Intermediate Similarity	NPC270507
0.7113	Intermediate Similarity	NPC288903
0.7107	Intermediate Similarity	NPC470816
0.7105	Intermediate Similarity	NPC217111
0.7105	Intermediate Similarity	NPC215419
0.7105	Intermediate Similarity	NPC186933
0.7105	Intermediate Similarity	NPC476357
0.7105	Intermediate Similarity	NPC93181
0.7094	Intermediate Similarity	NPC31296
0.7094	Intermediate Similarity	NPC258366
0.7094	Intermediate Similarity	NPC473974
0.7094	Intermediate Similarity	NPC79933
0.7094	Intermediate Similarity	NPC204784
0.7087	Intermediate Similarity	NPC238219
0.7083	Intermediate Similarity	NPC140118
0.7083	Intermediate Similarity	NPC473938
0.7083	Intermediate Similarity	NPC328107
0.7083	Intermediate Similarity	NPC12881
0.7075	Intermediate Similarity	NPC217621
0.7069	Intermediate Similarity	NPC152812
0.7069	Intermediate Similarity	NPC471926
0.7064	Intermediate Similarity	NPC321670
0.7064	Intermediate Similarity	NPC105899
0.7059	Intermediate Similarity	NPC269923
0.7059	Intermediate Similarity	NPC293831
0.7059	Intermediate Similarity	NPC369
0.7059	Intermediate Similarity	NPC167323
0.7059	Intermediate Similarity	NPC141607
0.7059	Intermediate Similarity	NPC133461
0.7059	Intermediate Similarity	NPC284475
0.7059	Intermediate Similarity	NPC187725
0.7059	Intermediate Similarity	NPC79917
0.7054	Intermediate Similarity	NPC474057
0.7048	Intermediate Similarity	NPC265220
0.7048	Intermediate Similarity	NPC324602
0.7048	Intermediate Similarity	NPC253423
0.7037	Intermediate Similarity	NPC274443
0.7037	Intermediate Similarity	NPC255676
0.7034	Intermediate Similarity	NPC318552
0.7034	Intermediate Similarity	NPC190501
0.703	Intermediate Similarity	NPC9822
0.7027	Intermediate Similarity	NPC318327
0.7019	Intermediate Similarity	NPC260233
0.7016	Intermediate Similarity	NPC475138
0.701	Intermediate Similarity	NPC103387
0.701	Intermediate Similarity	NPC323103
0.7009	Intermediate Similarity	NPC109514
0.7009	Intermediate Similarity	NPC254233
0.7009	Intermediate Similarity	NPC476993
0.7009	Intermediate Similarity	NPC289117
0.7008	Intermediate Similarity	NPC471864
0.7	Intermediate Similarity	NPC472699
0.7	Intermediate Similarity	NPC121168
0.7	Intermediate Similarity	NPC472700
0.7	Intermediate Similarity	NPC194326
0.699	Remote Similarity	NPC155232
0.699	Remote Similarity	NPC323420
0.6983	Remote Similarity	NPC470820
0.6983	Remote Similarity	NPC469843
0.6981	Remote Similarity	NPC476120
0.6981	Remote Similarity	NPC145052
0.6981	Remote Similarity	NPC229242
0.6979	Remote Similarity	NPC285716
0.6979	Remote Similarity	NPC17408
0.6979	Remote Similarity	NPC157055
0.6975	Remote Similarity	NPC164852
0.697	Remote Similarity	NPC294134
0.697	Remote Similarity	NPC475710
0.6967	Remote Similarity	NPC9180
0.6967	Remote Similarity	NPC100402
0.6961	Remote Similarity	NPC58872
0.696	Remote Similarity	NPC72915
0.6952	Remote Similarity	NPC219573
0.6952	Remote Similarity	NPC185208
0.6944	Remote Similarity	NPC244427

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 NPC469893 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
0.8229	Intermediate Similarity	NPD1088	Approved
0.8144	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.8021	Intermediate Similarity	NPD1089	Approved
0.8021	Intermediate Similarity	NPD1090	Approved
0.8021	Intermediate Similarity	NPD1086	Approved
0.7917	Intermediate Similarity	NPD5346	Phase 2
0.7917	Intermediate Similarity	NPD800	Approved
0.7917	Intermediate Similarity	NPD5347	Phase 2
0.7879	Intermediate Similarity	NPD1693	Approved
0.7826	Intermediate Similarity	NPD226	Approved
0.7745	Intermediate Similarity	NPD2066	Phase 3
0.7708	Intermediate Similarity	NPD1087	Approved
0.7708	Intermediate Similarity	NPD4793	Discontinued
0.7706	Intermediate Similarity	NPD6858	Approved
0.7706	Intermediate Similarity	NPD7094	Approved
0.77	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1239	Approved
0.7549	Intermediate Similarity	NPD1564	Approved
0.7549	Intermediate Similarity	NPD1565	Approved
0.7549	Intermediate Similarity	NPD1566	Phase 3
0.7524	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD1930	Approved
0.7524	Intermediate Similarity	NPD1929	Approved
0.75	Intermediate Similarity	NPD225	Approved
0.75	Intermediate Similarity	NPD227	Approved
0.75	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD3673	Approved
0.7475	Intermediate Similarity	NPD3672	Approved
0.7474	Intermediate Similarity	NPD9491	Approved
0.7456	Intermediate Similarity	NPD7009	Phase 2
0.7411	Intermediate Similarity	NPD5951	Approved
0.7368	Intermediate Similarity	NPD7610	Discontinued
0.7358	Intermediate Similarity	NPD5765	Approved
0.7353	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6049	Phase 2
0.7321	Intermediate Similarity	NPD6010	Discontinued
0.732	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6685	Approved
0.7282	Intermediate Similarity	NPD1989	Approved
0.7264	Intermediate Similarity	NPD1932	Approved
0.7257	Intermediate Similarity	NPD4766	Approved
0.7255	Intermediate Similarity	NPD1563	Approved
0.7212	Intermediate Similarity	NPD3495	Discontinued
0.7207	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD3642	Approved
0.7207	Intermediate Similarity	NPD3644	Approved
0.7207	Intermediate Similarity	NPD3643	Approved
0.7196	Intermediate Similarity	NPD6647	Phase 2
0.7182	Intermediate Similarity	NPD2329	Discontinued
0.7179	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2932	Approved
0.7157	Intermediate Similarity	NPD7631	Approved
0.713	Intermediate Similarity	NPD3797	Approved
0.713	Intermediate Similarity	NPD5909	Discontinued
0.7115	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD3971	Phase 1
0.7105	Intermediate Similarity	NPD2629	Approved
0.7059	Intermediate Similarity	NPD5618	Discontinued
0.7059	Intermediate Similarity	NPD7609	Phase 3
0.7053	Intermediate Similarity	NPD9490	Approved
0.7037	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD3019	Approved
0.7034	Intermediate Similarity	NPD4199	Phase 3
0.7009	Intermediate Similarity	NPD4479	Discontinued
0.7009	Intermediate Similarity	NPD3798	Phase 3
0.6981	Remote Similarity	NPD253	Approved
0.6964	Remote Similarity	NPD5278	Discontinued
0.6916	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5048	Discontinued
0.6905	Remote Similarity	NPD7961	Discontinued
0.687	Remote Similarity	NPD3598	Phase 3
0.6855	Remote Similarity	NPD5736	Approved
0.6842	Remote Similarity	NPD6912	Phase 3
0.6833	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD650	Approved
0.6814	Remote Similarity	NPD1317	Discontinued
0.6772	Remote Similarity	NPD6663	Approved
0.6762	Remote Similarity	NPD1066	Discontinued
0.6757	Remote Similarity	NPD1018	Approved
0.6724	Remote Similarity	NPD2652	Approved
0.6724	Remote Similarity	NPD2650	Approved
0.6694	Remote Similarity	NPD3026	Approved
0.6694	Remote Similarity	NPD3023	Approved
0.6693	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3025	Approved
0.6667	Remote Similarity	NPD4233	Approved
0.6667	Remote Similarity	NPD3024	Approved
0.6667	Remote Similarity	NPD4234	Approved
0.6667	Remote Similarity	NPD1508	Approved
0.6639	Remote Similarity	NPD6065	Approved
0.6638	Remote Similarity	NPD2607	Approved
0.6635	Remote Similarity	NPD9256	Approved
0.6635	Remote Similarity	NPD9258	Approved
0.6632	Remote Similarity	NPD9716	Approved
0.6614	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.661	Remote Similarity	NPD4198	Discontinued
0.6609	Remote Similarity	NPD5927	Discontinued
0.6606	Remote Similarity	NPD7798	Approved
0.6602	Remote Similarity	NPD1101	Approved
0.6587	Remote Similarity	NPD7084	Phase 3
0.6581	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD9566	Approved
0.6571	Remote Similarity	NPD5284	Approved
0.6571	Remote Similarity	NPD5281	Approved
0.6529	Remote Similarity	NPD5981	Approved
0.6522	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1752	Approved
0.6522	Remote Similarity	NPD1756	Approved
0.6515	Remote Similarity	NPD7305	Phase 1
0.6514	Remote Similarity	NPD5926	Approved
0.6514	Remote Similarity	NPD9495	Approved
0.6484	Remote Similarity	NPD7008	Discontinued
0.6481	Remote Similarity	NPD1843	Approved
0.6475	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD2345	Approved
0.6466	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD1067	Discontinued
0.6449	Remote Similarity	NPD720	Approved
0.6449	Remote Similarity	NPD719	Approved
0.6449	Remote Similarity	NPD1202	Approved
0.6429	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD7236	Approved
0.6417	Remote Similarity	NPD5162	Approved
0.6408	Remote Similarity	NPD9257	Approved
0.6408	Remote Similarity	NPD9259	Approved
0.6406	Remote Similarity	NPD7055	Discontinued
0.6404	Remote Similarity	NPD467	Phase 1
0.6393	Remote Similarity	NPD1855	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6994	Approved
0.6393	Remote Similarity	NPD6993	Approved
0.6389	Remote Similarity	NPD4814	Discontinued
0.6389	Remote Similarity	NPD4094	Approved
0.6385	Remote Similarity	NPD8032	Phase 2
0.6378	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD6085	Phase 2
0.6371	Remote Similarity	NPD4217	Approved
0.6371	Remote Similarity	NPD3131	Approved
0.6371	Remote Similarity	NPD2610	Approved
0.6371	Remote Similarity	NPD4215	Approved
0.6371	Remote Similarity	NPD3132	Approved
0.6371	Remote Similarity	NPD4216	Approved
0.6371	Remote Similarity	NPD4218	Approved
0.6371	Remote Similarity	NPD2608	Approved
0.6371	Remote Similarity	NPD2609	Approved
0.6371	Remote Similarity	NPD2612	Approved
0.6371	Remote Similarity	NPD2611	Approved
0.6355	Remote Similarity	NPD752	Approved
0.6349	Remote Similarity	NPD1283	Approved
0.6341	Remote Similarity	NPD4059	Approved
0.6341	Remote Similarity	NPD5306	Approved
0.6341	Remote Similarity	NPD5305	Approved
0.6333	Remote Similarity	NPD3317	Approved
0.6325	Remote Similarity	NPD188	Approved
0.6325	Remote Similarity	NPD189	Phase 3
0.632	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7741	Discontinued
0.6311	Remote Similarity	NPD3091	Approved
0.6311	Remote Similarity	NPD2617	Discontinued
0.6306	Remote Similarity	NPD3020	Approved
0.6303	Remote Similarity	NPD7077	Approved
0.6303	Remote Similarity	NPD7076	Approved
0.63	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD6565	Approved
0.6299	Remote Similarity	NPD6564	Approved
0.6299	Remote Similarity	NPD6563	Approved
0.6296	Remote Similarity	NPD1409	Phase 3
0.6296	Remote Similarity	NPD3719	Approved
0.6296	Remote Similarity	NPD3718	Approved
0.6293	Remote Similarity	NPD2182	Approved
0.629	Remote Similarity	NPD3881	Discontinued
0.629	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.629	Remote Similarity	NPD4879	Approved
0.6273	Remote Similarity	NPD4657	Approved
0.6273	Remote Similarity	NPD1875	Phase 1
0.6273	Remote Similarity	NPD4655	Approved
0.6261	Remote Similarity	NPD5705	Approved
0.6261	Remote Similarity	NPD5704	Approved
0.6261	Remote Similarity	NPD5706	Approved
0.626	Remote Similarity	NPD1245	Approved
0.626	Remote Similarity	NPD4102	Approved
0.626	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.626	Remote Similarity	NPD7715	Approved
0.626	Remote Similarity	NPD4105	Approved
0.626	Remote Similarity	NPD7714	Approved
0.626	Remote Similarity	NPD4163	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1246	Approved
0.625	Remote Similarity	NPD5280	Approved
0.625	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4694	Approved
0.624	Remote Similarity	NPD4806	Approved
0.624	Remote Similarity	NPD4807	Approved
0.6239	Remote Similarity	NPD2067	Discontinued
0.6239	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD942	Approved
0.623	Remote Similarity	NPD2116	Approved
0.623	Remote Similarity	NPD2115	Approved
0.623	Remote Similarity	NPD2117	Pre-registration
0.6228	Remote Similarity	NPD164	Approved
0.622	Remote Similarity	NPD6330	Clinical (unspecified phase)

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