NPASS Compound

Structure

NPC473434 OpenBabel07101718302D 23 25 0 0 1 0 0 0 0 0999 V2000 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -2.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 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 5 2 0 0 0 0 2 8 2 0 0 0 0 3 9 2 0 0 0 0 4 10 1 0 0 0 0 6 11 1 0 0 0 0 6 17 1 0 0 0 0 7 17 1 0 0 0 0 7 21 1 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 9 15 1 0 0 0 0 10 18 2 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 1 0 0 0 12 8 1 6 0 0 0 12 14 1 0 0 0 0 13 14 1 0 0 0 0 13 17 1 6 0 0 0 14 23 1 1 0 0 0 15 19 2 0 0 0 0 15 21 1 0 0 0 0 16 20 2 0 0 0 0 16 23 1 0 0 0 0 17 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.11
Volume:	313.841
LogP:	0.791
LogD:	1.068
LogS:	-2.868
# Rotatable Bonds:	3
TPSA:	78.9
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.331
Synthetic Accessibility Score:	4.87
Fsp3:	0.471
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.149
MDCK Permeability:	5.333270019036718e-05
Pgp-inhibitor:	0.954
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.303
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	64.0527572631836%
Volume Distribution (VD):	1.093
Pgp-substrate:	36.459049224853516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.264
CYP1A2-substrate:	0.084
CYP2C19-inhibitor:	0.126
CYP2C19-substrate:	0.256
CYP2C9-inhibitor:	0.165
CYP2C9-substrate:	0.041
CYP2D6-inhibitor:	0.172
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.692
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	2.6
Half-life (T1/2):	0.777

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.846
Drug-inuced Liver Injury (DILI):	0.66
AMES Toxicity:	0.147
Rat Oral Acute Toxicity:	0.853
Maximum Recommended Daily Dose:	0.795
Skin Sensitization:	0.835
Carcinogencity:	0.171
Eye Corrosion:	0.649
Eye Irritation:	0.569
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC473434

Natural Product ID:	NPC473434
*Common Name:**	Vernolepin Acetate
IUPAC Name:	[(3aR,4S,5aR,9aR,9bR)-5a-ethenyl-3,9-dimethylidene-2,8-dioxo-3a,4,5,6,9a,9b-hexahydrofuro[2,3-f]isochromen-4-yl] acetate
Synonyms:	Vernolepin Acetate
Standard InCHIKey:	ZYKHFUSRXBMQQA-GMIGGYDBSA-N
Standard InCHI:	InChI=1S/C17H18O6/c1-5-17-6-11(22-10(4)18)12-8(2)16(20)23-14(12)13(17)9(3)15(19)21-7-17/h5,11-14H,1-3,6-7H2,4H3/t11-,12+,13+,14-,17+/m0/s1
SMILES:	C=C[C@]12COC(=O)C(=C)[C@@H]2[C@@H]2[C@@H]([C@H](C1)OC(=O)C)C(=C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL430207
PubChem CID:	44444901
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic acids and derivatives

*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
NPO33469	Asteraceae	Family	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18329753]

☑ 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
ED50	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	pED50	=	5.07	n.a.	PMID[469193]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	2.7	ug ml-1	PMID[469193]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	8.49	umol/L	PMID[469194]

☑ 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 NPC473434 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	218
0.1-0.2	1422
0.2-0.3	4759
0.3-0.4	8286
0.4-0.5	13236
0.5-0.6	6291
0.6-0.7	6544
0.7-0.8	1794
0.8-0.85	98
0.85-0.9	29
0.9-0.95	15
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474841
1.0	High Similarity	NPC471446
0.9432	High Similarity	NPC475776
0.9341	High Similarity	NPC165528
0.9341	High Similarity	NPC228766
0.9255	High Similarity	NPC164551
0.9149	High Similarity	NPC242666
0.913	High Similarity	NPC284518
0.9091	High Similarity	NPC175293
0.9032	High Similarity	NPC474921
0.9022	High Similarity	NPC157686
0.9022	High Similarity	NPC259042
0.8947	High Similarity	NPC111292
0.8925	High Similarity	NPC473964
0.8913	High Similarity	NPC225474
0.8913	High Similarity	NPC148000
0.8913	High Similarity	NPC469596
0.8842	High Similarity	NPC47024
0.883	High Similarity	NPC473963
0.8817	High Similarity	NPC56369
0.875	High Similarity	NPC308824
0.8737	High Similarity	NPC476806
0.8737	High Similarity	NPC476807
0.8737	High Similarity	NPC216478
0.8723	High Similarity	NPC93245
0.871	High Similarity	NPC24861
0.8621	High Similarity	NPC38642
0.8587	High Similarity	NPC153853
0.8571	High Similarity	NPC156681
0.8557	High Similarity	NPC475958
0.8539	High Similarity	NPC470011
0.8523	High Similarity	NPC226988
0.8485	Intermediate Similarity	NPC477127
0.8478	Intermediate Similarity	NPC116620
0.8438	Intermediate Similarity	NPC136781
0.8421	Intermediate Similarity	NPC217329
0.8421	Intermediate Similarity	NPC90014
0.8384	Intermediate Similarity	NPC61442
0.8384	Intermediate Similarity	NPC254202
0.837	Intermediate Similarity	NPC477128
0.8333	Intermediate Similarity	NPC474243
0.8333	Intermediate Similarity	NPC469370
0.8333	Intermediate Similarity	NPC219011
0.8317	Intermediate Similarity	NPC284732
0.8317	Intermediate Similarity	NPC78966
0.8316	Intermediate Similarity	NPC477130
0.8316	Intermediate Similarity	NPC477129
0.8316	Intermediate Similarity	NPC66581
0.828	Intermediate Similarity	NPC194642
0.828	Intermediate Similarity	NPC73995
0.8265	Intermediate Similarity	NPC470761
0.8265	Intermediate Similarity	NPC473219
0.8261	Intermediate Similarity	NPC305029
0.8252	Intermediate Similarity	NPC253906
0.8247	Intermediate Similarity	NPC474395
0.8235	Intermediate Similarity	NPC37628
0.8222	Intermediate Similarity	NPC194637
0.8211	Intermediate Similarity	NPC475657
0.8202	Intermediate Similarity	NPC47635
0.82	Intermediate Similarity	NPC99510
0.8191	Intermediate Similarity	NPC152467
0.8172	Intermediate Similarity	NPC215831
0.8152	Intermediate Similarity	NPC85698
0.8152	Intermediate Similarity	NPC9231
0.8152	Intermediate Similarity	NPC185638
0.8137	Intermediate Similarity	NPC180744
0.8105	Intermediate Similarity	NPC186363
0.8105	Intermediate Similarity	NPC233345
0.8105	Intermediate Similarity	NPC473944
0.8105	Intermediate Similarity	NPC165180
0.81	Intermediate Similarity	NPC476081
0.8085	Intermediate Similarity	NPC288699
0.8065	Intermediate Similarity	NPC181103
0.8065	Intermediate Similarity	NPC470012
0.8061	Intermediate Similarity	NPC70145
0.8061	Intermediate Similarity	NPC91695
0.8058	Intermediate Similarity	NPC189075
0.8058	Intermediate Similarity	NPC275539
0.8039	Intermediate Similarity	NPC469607
0.8037	Intermediate Similarity	NPC477509
0.8037	Intermediate Similarity	NPC270478
0.8021	Intermediate Similarity	NPC147272
0.802	Intermediate Similarity	NPC72842
0.8	Intermediate Similarity	NPC475951
0.8	Intermediate Similarity	NPC158488
0.7981	Intermediate Similarity	NPC112457
0.798	Intermediate Similarity	NPC38471
0.798	Intermediate Similarity	NPC89099
0.798	Intermediate Similarity	NPC28864
0.798	Intermediate Similarity	NPC20479
0.798	Intermediate Similarity	NPC469986
0.798	Intermediate Similarity	NPC38296
0.798	Intermediate Similarity	NPC98837
0.798	Intermediate Similarity	NPC162459
0.7961	Intermediate Similarity	NPC110496
0.7959	Intermediate Similarity	NPC307164
0.7957	Intermediate Similarity	NPC477920
0.7941	Intermediate Similarity	NPC283850
0.7941	Intermediate Similarity	NPC470297
0.7938	Intermediate Similarity	NPC470697
0.7938	Intermediate Similarity	NPC250075
0.7938	Intermediate Similarity	NPC476722
0.7935	Intermediate Similarity	NPC97505
0.7935	Intermediate Similarity	NPC159635
0.7921	Intermediate Similarity	NPC469606
0.7921	Intermediate Similarity	NPC273005
0.7921	Intermediate Similarity	NPC31058
0.7921	Intermediate Similarity	NPC58329
0.7921	Intermediate Similarity	NPC162973
0.7921	Intermediate Similarity	NPC170615
0.7917	Intermediate Similarity	NPC476934
0.7912	Intermediate Similarity	NPC178676
0.7905	Intermediate Similarity	NPC472666
0.7905	Intermediate Similarity	NPC5103
0.79	Intermediate Similarity	NPC293866
0.79	Intermediate Similarity	NPC471413
0.79	Intermediate Similarity	NPC477656
0.7879	Intermediate Similarity	NPC38530
0.7879	Intermediate Similarity	NPC111348
0.7879	Intermediate Similarity	NPC472188
0.7879	Intermediate Similarity	NPC96839
0.7879	Intermediate Similarity	NPC10864
0.7879	Intermediate Similarity	NPC84335
0.7857	Intermediate Similarity	NPC183012
0.785	Intermediate Similarity	NPC477126
0.785	Intermediate Similarity	NPC470120
0.785	Intermediate Similarity	NPC25909
0.7849	Intermediate Similarity	NPC110405
0.7843	Intermediate Similarity	NPC120321
0.7843	Intermediate Similarity	NPC471364
0.7843	Intermediate Similarity	NPC471365
0.7843	Intermediate Similarity	NPC132395
0.7841	Intermediate Similarity	NPC92489
0.783	Intermediate Similarity	NPC474846
0.783	Intermediate Similarity	NPC469655
0.783	Intermediate Similarity	NPC304180
0.783	Intermediate Similarity	NPC179798
0.783	Intermediate Similarity	NPC469656
0.7822	Intermediate Similarity	NPC46848
0.7822	Intermediate Similarity	NPC471412
0.78	Intermediate Similarity	NPC474793
0.78	Intermediate Similarity	NPC318917
0.78	Intermediate Similarity	NPC471366
0.78	Intermediate Similarity	NPC252295
0.78	Intermediate Similarity	NPC476800
0.78	Intermediate Similarity	NPC472186
0.78	Intermediate Similarity	NPC474724
0.78	Intermediate Similarity	NPC23364
0.7798	Intermediate Similarity	NPC469684
0.7789	Intermediate Similarity	NPC226863
0.7789	Intermediate Similarity	NPC277771
0.7788	Intermediate Similarity	NPC133422
0.7788	Intermediate Similarity	NPC67321
0.7788	Intermediate Similarity	NPC302788
0.7788	Intermediate Similarity	NPC187435
0.7778	Intermediate Similarity	NPC202833
0.7778	Intermediate Similarity	NPC200054
0.7778	Intermediate Similarity	NPC256227
0.7778	Intermediate Similarity	NPC234993
0.7778	Intermediate Similarity	NPC90472
0.7778	Intermediate Similarity	NPC29410
0.7778	Intermediate Similarity	NPC134072
0.7767	Intermediate Similarity	NPC146731
0.7757	Intermediate Similarity	NPC269530
0.7757	Intermediate Similarity	NPC265391
0.7757	Intermediate Similarity	NPC12046
0.7757	Intermediate Similarity	NPC194951
0.7757	Intermediate Similarity	NPC222834
0.7755	Intermediate Similarity	NPC57117
0.7755	Intermediate Similarity	NPC100257
0.7755	Intermediate Similarity	NPC224410
0.7745	Intermediate Similarity	NPC286519
0.7745	Intermediate Similarity	NPC148628
0.7745	Intermediate Similarity	NPC275990
0.7745	Intermediate Similarity	NPC214946
0.7745	Intermediate Similarity	NPC88203
0.7745	Intermediate Similarity	NPC76866
0.7745	Intermediate Similarity	NPC246736
0.7745	Intermediate Similarity	NPC304832
0.7742	Intermediate Similarity	NPC139566
0.7736	Intermediate Similarity	NPC124053
0.7736	Intermediate Similarity	NPC478209
0.7732	Intermediate Similarity	NPC49420
0.7732	Intermediate Similarity	NPC72845
0.7732	Intermediate Similarity	NPC470230
0.7727	Intermediate Similarity	NPC284707
0.7723	Intermediate Similarity	NPC287676
0.7723	Intermediate Similarity	NPC476303
0.7723	Intermediate Similarity	NPC472187
0.7723	Intermediate Similarity	NPC267921
0.7723	Intermediate Similarity	NPC473204
0.7723	Intermediate Similarity	NPC477655
0.7723	Intermediate Similarity	NPC473545
0.7723	Intermediate Similarity	NPC470906
0.7723	Intermediate Similarity	NPC476933
0.7714	Intermediate Similarity	NPC476479
0.7714	Intermediate Similarity	NPC476802
0.7714	Intermediate Similarity	NPC89171
0.7708	Intermediate Similarity	NPC471043
0.77	Intermediate Similarity	NPC110937

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 NPC473434 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	1739
0.2-0.3	3872
0.3-0.4	2150
0.4-0.5	734
0.5-0.6	237
0.6-0.7	184
0.7-0.8	50
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.766	Intermediate Similarity	NPD1694	Approved
0.7547	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD6008	Approved
0.734	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7638	Approved
0.7282	Intermediate Similarity	NPD4225	Approved
0.7212	Intermediate Similarity	NPD7639	Approved
0.7212	Intermediate Similarity	NPD7640	Approved
0.7143	Intermediate Similarity	NPD3573	Approved
0.7091	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6686	Approved
0.7059	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7900	Approved
0.703	Intermediate Similarity	NPD8035	Phase 2
0.703	Intermediate Similarity	NPD8034	Phase 2
0.7	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1695	Approved
0.699	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5697	Approved
0.6961	Remote Similarity	NPD6399	Phase 3
0.6939	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6881	Approved
0.6909	Remote Similarity	NPD6899	Approved
0.6875	Remote Similarity	NPD6650	Approved
0.6875	Remote Similarity	NPD6649	Approved
0.687	Remote Similarity	NPD7115	Discovery
0.6857	Remote Similarity	NPD7902	Approved
0.6847	Remote Similarity	NPD6013	Approved
0.6847	Remote Similarity	NPD6014	Approved
0.6847	Remote Similarity	NPD6012	Approved
0.6786	Remote Similarity	NPD7290	Approved
0.6786	Remote Similarity	NPD6883	Approved
0.6786	Remote Similarity	NPD7102	Approved
0.678	Remote Similarity	NPD6921	Approved
0.6757	Remote Similarity	NPD6011	Approved
0.6754	Remote Similarity	NPD8133	Approved
0.6754	Remote Similarity	NPD4632	Approved
0.6731	Remote Similarity	NPD7748	Approved
0.6731	Remote Similarity	NPD5282	Discontinued
0.6729	Remote Similarity	NPD6648	Approved
0.6727	Remote Similarity	NPD6402	Approved
0.6727	Remote Similarity	NPD7128	Approved
0.6727	Remote Similarity	NPD5739	Approved
0.6727	Remote Similarity	NPD6675	Approved
0.6726	Remote Similarity	NPD6869	Approved
0.6726	Remote Similarity	NPD6847	Approved
0.6726	Remote Similarity	NPD6617	Approved
0.6726	Remote Similarity	NPD8130	Phase 1
0.67	Remote Similarity	NPD7146	Approved
0.67	Remote Similarity	NPD6409	Approved
0.67	Remote Similarity	NPD7334	Approved
0.67	Remote Similarity	NPD7521	Approved
0.67	Remote Similarity	NPD6684	Approved
0.67	Remote Similarity	NPD5330	Approved
0.6699	Remote Similarity	NPD6411	Approved
0.6696	Remote Similarity	NPD6372	Approved
0.6696	Remote Similarity	NPD6373	Approved
0.6695	Remote Similarity	NPD6319	Approved
0.6694	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6635	Remote Similarity	NPD5779	Approved
0.6635	Remote Similarity	NPD5778	Approved
0.6612	Remote Similarity	NPD7492	Approved
0.6607	Remote Similarity	NPD7320	Approved
0.6606	Remote Similarity	NPD5211	Phase 2
0.6606	Remote Similarity	NPD7632	Discontinued
0.6602	Remote Similarity	NPD46	Approved
0.6602	Remote Similarity	NPD6698	Approved
0.66	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6009	Approved
0.6574	Remote Similarity	NPD5286	Approved
0.6574	Remote Similarity	NPD5285	Approved
0.6574	Remote Similarity	NPD4696	Approved
0.6569	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6672	Approved
0.6569	Remote Similarity	NPD5737	Approved
0.6569	Remote Similarity	NPD6903	Approved
0.6557	Remote Similarity	NPD6616	Approved
0.6555	Remote Similarity	NPD6054	Approved
0.6538	Remote Similarity	NPD7515	Phase 2
0.6538	Remote Similarity	NPD5693	Phase 1
0.6538	Remote Similarity	NPD6079	Approved
0.6535	Remote Similarity	NPD3618	Phase 1
0.6522	Remote Similarity	NPD6053	Discontinued
0.6505	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6101	Approved
0.6504	Remote Similarity	NPD7078	Approved
0.65	Remote Similarity	NPD8515	Approved
0.65	Remote Similarity	NPD6015	Approved
0.65	Remote Similarity	NPD5983	Phase 2
0.65	Remote Similarity	NPD6016	Approved
0.65	Remote Similarity	NPD8517	Approved
0.65	Remote Similarity	NPD8516	Approved
0.65	Remote Similarity	NPD8513	Phase 3
0.6486	Remote Similarity	NPD5141	Approved
0.6455	Remote Similarity	NPD5226	Approved
0.6455	Remote Similarity	NPD5224	Approved
0.6455	Remote Similarity	NPD4633	Approved
0.6455	Remote Similarity	NPD5225	Approved
0.6452	Remote Similarity	NPD7736	Approved
0.6449	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5221	Approved
0.6449	Remote Similarity	NPD5222	Approved
0.6446	Remote Similarity	NPD6370	Approved
0.6446	Remote Similarity	NPD5988	Approved
0.6442	Remote Similarity	NPD5207	Approved
0.6429	Remote Similarity	NPD7260	Phase 2
0.6415	Remote Similarity	NPD6001	Approved
0.6404	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD5174	Approved
0.6396	Remote Similarity	NPD5175	Approved
0.6393	Remote Similarity	NPD8328	Phase 3
0.6393	Remote Similarity	NPD7604	Phase 2
0.6389	Remote Similarity	NPD4755	Approved
0.6389	Remote Similarity	NPD5173	Approved
0.6387	Remote Similarity	NPD7328	Approved
0.6387	Remote Similarity	NPD7327	Approved
0.6381	Remote Similarity	NPD7637	Suspended
0.6372	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6412	Phase 2
0.6364	Remote Similarity	NPD5223	Approved
0.6364	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD6274	Approved
0.6355	Remote Similarity	NPD5695	Phase 3
0.6348	Remote Similarity	NPD6371	Approved
0.6348	Remote Similarity	NPD4634	Approved
0.6346	Remote Similarity	NPD5328	Approved
0.6337	Remote Similarity	NPD3668	Phase 3
0.6333	Remote Similarity	NPD7101	Approved
0.6333	Remote Similarity	NPD7516	Approved
0.6333	Remote Similarity	NPD7100	Approved
0.633	Remote Similarity	NPD5696	Approved
0.6303	Remote Similarity	NPD6317	Approved
0.6303	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.63	Remote Similarity	NPD3667	Approved
0.6296	Remote Similarity	NPD4697	Phase 3
0.6293	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6336	Discontinued
0.6286	Remote Similarity	NPD5785	Approved
0.6281	Remote Similarity	NPD6059	Approved
0.6273	Remote Similarity	NPD4700	Approved
0.625	Remote Similarity	NPD6335	Approved
0.625	Remote Similarity	NPD6313	Approved
0.625	Remote Similarity	NPD8039	Approved
0.625	Remote Similarity	NPD6314	Approved
0.624	Remote Similarity	NPD8074	Phase 3
0.624	Remote Similarity	NPD8293	Discontinued
0.6239	Remote Similarity	NPD6084	Phase 2
0.6239	Remote Similarity	NPD6083	Phase 2
0.623	Remote Similarity	NPD8335	Approved
0.623	Remote Similarity	NPD8033	Approved
0.623	Remote Similarity	NPD8296	Approved
0.623	Remote Similarity	NPD8380	Approved
0.623	Remote Similarity	NPD8378	Approved
0.623	Remote Similarity	NPD7503	Approved
0.623	Remote Similarity	NPD8379	Approved
0.6226	Remote Similarity	NPD5284	Approved
0.6226	Remote Similarity	NPD5694	Approved
0.6226	Remote Similarity	NPD5281	Approved
0.6224	Remote Similarity	NPD6114	Approved
0.6224	Remote Similarity	NPD6115	Approved
0.6224	Remote Similarity	NPD6697	Approved
0.6224	Remote Similarity	NPD6118	Approved
0.6218	Remote Similarity	NPD6868	Approved
0.62	Remote Similarity	NPD1779	Approved
0.62	Remote Similarity	NPD1780	Approved
0.619	Remote Similarity	NPD6051	Approved
0.619	Remote Similarity	NPD6080	Approved
0.619	Remote Similarity	NPD6904	Approved
0.619	Remote Similarity	NPD6673	Approved
0.6182	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD4786	Approved
0.6174	Remote Similarity	NPD4730	Approved
0.6174	Remote Similarity	NPD4729	Approved
0.6168	Remote Similarity	NPD4202	Approved
0.6148	Remote Similarity	NPD8294	Approved
0.6148	Remote Similarity	NPD8377	Approved
0.6147	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5209	Approved
0.6132	Remote Similarity	NPD7838	Discovery
0.6132	Remote Similarity	NPD5692	Phase 3
0.6124	Remote Similarity	NPD6845	Suspended
0.6122	Remote Similarity	NPD6116	Phase 1
0.6095	Remote Similarity	NPD5208	Approved
0.6075	Remote Similarity	NPD7983	Approved
0.6075	Remote Similarity	NPD6050	Approved
0.6071	Remote Similarity	NPD1700	Approved
0.6068	Remote Similarity	NPD5247	Approved
0.6068	Remote Similarity	NPD5248	Approved
0.6068	Remote Similarity	NPD5250	Approved
0.6068	Remote Similarity	NPD5249	Phase 3
0.6068	Remote Similarity	NPD5251	Approved
0.6058	Remote Similarity	NPD6098	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