NPASS Compound

Structure

CID324017 OpenBabel06191716172D 34 35 0 0 1 0 0 0 0 0999 V2000 0.9454 -5.9953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7811 1.3963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2238 -3.6789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3890 2.9098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3321 -3.7007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 -2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2947 1.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6886 -5.3261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1933 2.2053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6685 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4697 -0.2263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4807 -4.3480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1988 2.1007 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.9254 -2.7872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8765 -1.1399 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9309 -2.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0649 -2.3917 0.0000 C 0 0 1 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 1.6092 0.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5296 -4.0390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 1.1872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6037 0.2737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8710 -1.0354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7230 -3.8698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2135 -4.7081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3799 0.3782 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2728 1.0168 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3217 -3.0608 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 1.2024 1.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 9 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 6 15 2 0 0 0 0 8 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 10 16 1 0 0 0 0 11 16 1 0 0 0 0 11 25 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 5 1 6 0 0 0 14 18 1 0 0 0 0 15 24 1 0 0 0 0 16 26 1 1 0 0 0 17 15 1 6 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 18 27 2 0 0 0 0 19 32 1 1 0 0 0 20 21 1 0 0 0 0 20 33 1 1 0 0 0 21 25 1 6 0 0 0 21 34 1 0 0 0 0 22 28 2 0 0 0 0 22 32 1 0 0 0 0 23 29 2 0 0 0 0 23 34 1 0 0 0 0 24 30 2 0 0 0 0 24 33 1 0 0 0 0 25 7 1 6 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.24
Volume:	487.136
LogP:	1.615
LogD:	0.865
LogS:	-2.095
# Rotatable Bonds:	7
TPSA:	136.43
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.344
Synthetic Accessibility Score:	5.413
Fsp3:	0.68
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.833
MDCK Permeability:	8.331019489560276e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.114
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.111
Plasma Protein Binding (PPB):	71.74261474609375%
Volume Distribution (VD):	0.973
Pgp-substrate:	25.14573860168457%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.209
CYP2C19-inhibitor:	0.087
CYP2C19-substrate:	0.645
CYP2C9-inhibitor:	0.298
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.038
CYP3A4-inhibitor:	0.895
CYP3A4-substrate:	0.371

ADMET: Excretion

Clearance (CL):	10.344
Half-life (T1/2):	0.759

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.956
Drug-inuced Liver Injury (DILI):	0.907
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.389
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.274
Carcinogencity:	0.141
Eye Corrosion:	0.246
Eye Irritation:	0.037
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC324017

Natural Product ID:	NPC324017
*Common Name:**	Cardivin A
IUPAC Name:	[(3aR,4S,6S,8S,10S,11S,11aR)-8,10-dihydroxy-6,10-dimethyl-4-[(Z)-2-methylbut-2-enoyl]oxy-3-methylidene-2,5-dioxo-3a,4,6,7,8,9,11,11a-octahydrocyclodeca[b]furan-11-yl] 2-methylbutanoate
Synonyms:
Standard InCHIKey:	NAOJFCUVTXMIRE-ZOANBUIWSA-N
Standard InCHI:	InChI=1S/C25H36O9/c1-8-12(3)22(28)32-19-17-15(6)24(30)33-20(17)21(34-23(29)13(4)9-2)25(7,31)11-16(26)10-14(5)18(19)27/h8,13-14,16-17,19-21,26,31H,6,9-11H2,1-5,7H3/b12-8-/t13?,14-,16-,17-,19-,20+,21-,25-/m0/s1
SMILES:	CCC(C)C(=O)OC1C2C(C(C(=O)C(CC(CC1(C)O)O)C)OC(=O)C(=CC)C)C(=C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458848
PubChem CID:	21582598
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides 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
NPO9396	Carpesium divaricatum	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[9392887]
NPO9396	Carpesium divaricatum	Species	Asteraceae	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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	3.17	ug ml-1	PMID[542020]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	1.47	ug ml-1	PMID[542020]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	1.16	ug ml-1	PMID[542020]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	1.4	ug ml-1	PMID[542020]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	1.28	ug ml-1	PMID[542020]

☑ 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 NPC324017 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	254
0.1-0.2	1619
0.2-0.3	5515
0.3-0.4	9554
0.4-0.5	14271
0.5-0.6	7317
0.6-0.7	3285
0.7-0.8	764
0.8-0.85	81
0.85-0.9	18
0.9-0.95	13
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC320019
0.9894	High Similarity	NPC15993
0.9574	High Similarity	NPC323421
0.9574	High Similarity	NPC328562
0.9468	High Similarity	NPC31645
0.9255	High Similarity	NPC190294
0.9082	High Similarity	NPC476270
0.9082	High Similarity	NPC201718
0.9062	High Similarity	NPC470883
0.9062	High Similarity	NPC158416
0.9062	High Similarity	NPC39859
0.9062	High Similarity	NPC76862
0.8812	High Similarity	NPC472756
0.88	High Similarity	NPC149371
0.8763	High Similarity	NPC36954
0.875	High Similarity	NPC476300
0.8713	High Similarity	NPC472755
0.87	High Similarity	NPC47880
0.8687	High Similarity	NPC474213
0.8687	High Similarity	NPC471144
0.8646	High Similarity	NPC30515
0.8646	High Similarity	NPC184463
0.8641	High Similarity	NPC477513
0.8614	High Similarity	NPC472754
0.8557	High Similarity	NPC475912
0.8542	High Similarity	NPC51004
0.8529	High Similarity	NPC475945
0.8529	High Similarity	NPC475871
0.8515	High Similarity	NPC474339
0.8515	High Similarity	NPC164598
0.8515	High Similarity	NPC472753
0.8485	Intermediate Similarity	NPC476009
0.8485	Intermediate Similarity	NPC476315
0.8447	Intermediate Similarity	NPC472748
0.8438	Intermediate Similarity	NPC173926
0.8438	Intermediate Similarity	NPC307411
0.8438	Intermediate Similarity	NPC92974
0.8438	Intermediate Similarity	NPC474951
0.8431	Intermediate Similarity	NPC474747
0.8416	Intermediate Similarity	NPC475949
0.8384	Intermediate Similarity	NPC270013
0.8384	Intermediate Similarity	NPC475900
0.8384	Intermediate Similarity	NPC14961
0.8367	Intermediate Similarity	NPC273579
0.8367	Intermediate Similarity	NPC179746
0.8367	Intermediate Similarity	NPC162205
0.8367	Intermediate Similarity	NPC288240
0.8367	Intermediate Similarity	NPC81419
0.8367	Intermediate Similarity	NPC212486
0.8367	Intermediate Similarity	NPC295204
0.8365	Intermediate Similarity	NPC472751
0.8365	Intermediate Similarity	NPC472749
0.8351	Intermediate Similarity	NPC474761
0.8351	Intermediate Similarity	NPC476004
0.8351	Intermediate Similarity	NPC473619
0.835	Intermediate Similarity	NPC475873
0.835	Intermediate Similarity	NPC472750
0.835	Intermediate Similarity	NPC472747
0.8333	Intermediate Similarity	NPC474742
0.8333	Intermediate Similarity	NPC202672
0.8333	Intermediate Similarity	NPC46998
0.8333	Intermediate Similarity	NPC133907
0.8333	Intermediate Similarity	NPC185141
0.8333	Intermediate Similarity	NPC58219
0.8333	Intermediate Similarity	NPC110443
0.8333	Intermediate Similarity	NPC177629
0.8333	Intermediate Similarity	NPC128733
0.8317	Intermediate Similarity	NPC473326
0.8302	Intermediate Similarity	NPC38154
0.83	Intermediate Similarity	NPC279621
0.8283	Intermediate Similarity	NPC81386
0.8283	Intermediate Similarity	NPC474035
0.8269	Intermediate Similarity	NPC474741
0.8265	Intermediate Similarity	NPC329952
0.8265	Intermediate Similarity	NPC475881
0.8265	Intermediate Similarity	NPC70251
0.8265	Intermediate Similarity	NPC473321
0.8265	Intermediate Similarity	NPC12172
0.8265	Intermediate Similarity	NPC208886
0.8252	Intermediate Similarity	NPC471148
0.8235	Intermediate Similarity	NPC288876
0.8229	Intermediate Similarity	NPC186148
0.82	Intermediate Similarity	NPC471142
0.82	Intermediate Similarity	NPC474947
0.8191	Intermediate Similarity	NPC128429
0.8182	Intermediate Similarity	NPC475302
0.8163	Intermediate Similarity	NPC475748
0.8163	Intermediate Similarity	NPC469718
0.8163	Intermediate Similarity	NPC329857
0.8155	Intermediate Similarity	NPC264477
0.8155	Intermediate Similarity	NPC477511
0.8125	Intermediate Similarity	NPC475019
0.8125	Intermediate Similarity	NPC476015
0.8125	Intermediate Similarity	NPC474949
0.8125	Intermediate Similarity	NPC474762
0.8119	Intermediate Similarity	NPC473859
0.8119	Intermediate Similarity	NPC17585
0.8105	Intermediate Similarity	NPC151176
0.8105	Intermediate Similarity	NPC3464
0.8105	Intermediate Similarity	NPC474780
0.8105	Intermediate Similarity	NPC475963
0.81	Intermediate Similarity	NPC121825
0.81	Intermediate Similarity	NPC57405
0.81	Intermediate Similarity	NPC303942
0.81	Intermediate Similarity	NPC474247
0.8095	Intermediate Similarity	NPC100487
0.8073	Intermediate Similarity	NPC66108
0.8061	Intermediate Similarity	NPC474032
0.8041	Intermediate Similarity	NPC179659
0.8041	Intermediate Similarity	NPC5130
0.8039	Intermediate Similarity	NPC40812
0.8021	Intermediate Similarity	NPC149725
0.8021	Intermediate Similarity	NPC304509
0.8021	Intermediate Similarity	NPC329749
0.8021	Intermediate Similarity	NPC47958
0.802	Intermediate Similarity	NPC471141
0.802	Intermediate Similarity	NPC475659
0.8	Intermediate Similarity	NPC4620
0.8	Intermediate Similarity	NPC469645
0.8	Intermediate Similarity	NPC125674
0.8	Intermediate Similarity	NPC475838
0.8	Intermediate Similarity	NPC228451
0.8	Intermediate Similarity	NPC469692
0.798	Intermediate Similarity	NPC475855
0.798	Intermediate Similarity	NPC179394
0.798	Intermediate Similarity	NPC144133
0.798	Intermediate Similarity	NPC65359
0.798	Intermediate Similarity	NPC251385
0.798	Intermediate Similarity	NPC49342
0.7961	Intermediate Similarity	NPC187268
0.7959	Intermediate Similarity	NPC473715
0.7946	Intermediate Similarity	NPC471145
0.7946	Intermediate Similarity	NPC471146
0.7944	Intermediate Similarity	NPC324327
0.7944	Intermediate Similarity	NPC72813
0.7944	Intermediate Similarity	NPC326994
0.7944	Intermediate Similarity	NPC26617
0.7944	Intermediate Similarity	NPC474421
0.7944	Intermediate Similarity	NPC194620
0.7941	Intermediate Similarity	NPC476275
0.7941	Intermediate Similarity	NPC230800
0.7941	Intermediate Similarity	NPC477921
0.7925	Intermediate Similarity	NPC203659
0.7925	Intermediate Similarity	NPC220964
0.7925	Intermediate Similarity	NPC471143
0.7925	Intermediate Similarity	NPC475676
0.7925	Intermediate Similarity	NPC477510
0.7921	Intermediate Similarity	NPC473330
0.7921	Intermediate Similarity	NPC473316
0.7905	Intermediate Similarity	NPC197835
0.7905	Intermediate Similarity	NPC189609
0.7905	Intermediate Similarity	NPC291500
0.7905	Intermediate Similarity	NPC140591
0.7905	Intermediate Similarity	NPC303653
0.79	Intermediate Similarity	NPC20713
0.789	Intermediate Similarity	NPC5103
0.7885	Intermediate Similarity	NPC477512
0.7879	Intermediate Similarity	NPC166919
0.7879	Intermediate Similarity	NPC280612
0.7879	Intermediate Similarity	NPC477011
0.7879	Intermediate Similarity	NPC295312
0.7879	Intermediate Similarity	NPC477017
0.7879	Intermediate Similarity	NPC151770
0.7879	Intermediate Similarity	NPC477016
0.7876	Intermediate Similarity	NPC475401
0.787	Intermediate Similarity	NPC474664
0.787	Intermediate Similarity	NPC14862
0.787	Intermediate Similarity	NPC327286
0.787	Intermediate Similarity	NPC55972
0.787	Intermediate Similarity	NPC233379
0.787	Intermediate Similarity	NPC169888
0.7864	Intermediate Similarity	NPC471140
0.7857	Intermediate Similarity	NPC231889
0.7857	Intermediate Similarity	NPC248602
0.785	Intermediate Similarity	NPC223450
0.785	Intermediate Similarity	NPC9303
0.785	Intermediate Similarity	NPC243998
0.785	Intermediate Similarity	NPC16313
0.785	Intermediate Similarity	NPC54737
0.7843	Intermediate Similarity	NPC477922
0.7838	Intermediate Similarity	NPC469463
0.7838	Intermediate Similarity	NPC469454
0.7838	Intermediate Similarity	NPC469496
0.7835	Intermediate Similarity	NPC21469
0.7835	Intermediate Similarity	NPC137033
0.783	Intermediate Similarity	NPC110989
0.783	Intermediate Similarity	NPC475321
0.7822	Intermediate Similarity	NPC165383
0.7812	Intermediate Similarity	NPC11620
0.781	Intermediate Similarity	NPC473332
0.7807	Intermediate Similarity	NPC477092
0.78	Intermediate Similarity	NPC206614
0.78	Intermediate Similarity	NPC474323
0.78	Intermediate Similarity	NPC473448
0.7798	Intermediate Similarity	NPC475922
0.7798	Intermediate Similarity	NPC15218
0.7798	Intermediate Similarity	NPC139838
0.7798	Intermediate Similarity	NPC59489
0.7788	Intermediate Similarity	NPC308567
0.7788	Intermediate Similarity	NPC161855

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 NPC324017 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	271
0.1-0.2	2318
0.2-0.3	3709
0.3-0.4	1863
0.4-0.5	662
0.5-0.6	242
0.6-0.7	82
0.7-0.8	3
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
0.7944	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD46	Approved
0.78	Intermediate Similarity	NPD6698	Approved
0.7475	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7838	Discovery
0.7411	Intermediate Similarity	NPD6371	Approved
0.7379	Intermediate Similarity	NPD7983	Approved
0.7345	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6686	Approved
0.6972	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5282	Discontinued
0.6721	Remote Similarity	NPD6319	Approved
0.6719	Remote Similarity	NPD7260	Phase 2
0.6698	Remote Similarity	NPD1695	Approved
0.6696	Remote Similarity	NPD5344	Discontinued
0.6695	Remote Similarity	NPD6053	Discontinued
0.6695	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6636	Remote Similarity	NPD5785	Approved
0.661	Remote Similarity	NPD6649	Approved
0.661	Remote Similarity	NPD6650	Approved
0.6602	Remote Similarity	NPD6110	Phase 1
0.6581	Remote Similarity	NPD6372	Approved
0.6581	Remote Similarity	NPD6373	Approved
0.656	Remote Similarity	NPD7642	Approved
0.6538	Remote Similarity	NPD6845	Suspended
0.6514	Remote Similarity	NPD5778	Approved
0.6514	Remote Similarity	NPD5779	Approved
0.6508	Remote Similarity	NPD7492	Approved
0.6505	Remote Similarity	NPD6435	Approved
0.65	Remote Similarity	NPD4632	Approved
0.6496	Remote Similarity	NPD6881	Approved
0.6496	Remote Similarity	NPD6899	Approved
0.6476	Remote Similarity	NPD5363	Approved
0.6475	Remote Similarity	NPD7115	Discovery
0.6466	Remote Similarity	NPD5739	Approved
0.6466	Remote Similarity	NPD7128	Approved
0.6466	Remote Similarity	NPD6675	Approved
0.6466	Remote Similarity	NPD6402	Approved
0.6457	Remote Similarity	NPD7507	Approved
0.6457	Remote Similarity	NPD6616	Approved
0.6452	Remote Similarity	NPD6054	Approved
0.6442	Remote Similarity	NPD7154	Phase 3
0.6429	Remote Similarity	NPD8328	Phase 3
0.6423	Remote Similarity	NPD7641	Discontinued
0.6417	Remote Similarity	NPD6882	Approved
0.6415	Remote Similarity	NPD5786	Approved
0.641	Remote Similarity	NPD5697	Approved
0.6406	Remote Similarity	NPD8074	Phase 3
0.6406	Remote Similarity	NPD7078	Approved
0.64	Remote Similarity	NPD8444	Approved
0.6387	Remote Similarity	NPD7102	Approved
0.6387	Remote Similarity	NPD7290	Approved
0.6387	Remote Similarity	NPD6883	Approved
0.6372	Remote Similarity	NPD5696	Approved
0.6357	Remote Similarity	NPD7736	Approved
0.6356	Remote Similarity	NPD7320	Approved
0.6355	Remote Similarity	NPD4251	Approved
0.6355	Remote Similarity	NPD4250	Approved
0.6349	Remote Similarity	NPD8080	Discontinued
0.6349	Remote Similarity	NPD6370	Approved
0.6341	Remote Similarity	NPD6009	Approved
0.6339	Remote Similarity	NPD7839	Suspended
0.6333	Remote Similarity	NPD6617	Approved
0.6333	Remote Similarity	NPD6847	Approved
0.6333	Remote Similarity	NPD8130	Phase 1
0.6333	Remote Similarity	NPD6869	Approved
0.632	Remote Similarity	NPD6059	Approved
0.6316	Remote Similarity	NPD6648	Approved
0.6311	Remote Similarity	NPD5368	Approved
0.6308	Remote Similarity	NPD7319	Approved
0.6303	Remote Similarity	NPD6012	Approved
0.6303	Remote Similarity	NPD6013	Approved
0.6303	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD6014	Approved
0.6299	Remote Similarity	NPD7604	Phase 2
0.6299	Remote Similarity	NPD7830	Approved
0.6299	Remote Similarity	NPD7829	Approved
0.6283	Remote Similarity	NPD6084	Phase 2
0.6283	Remote Similarity	NPD6083	Phase 2
0.6279	Remote Similarity	NPD8293	Discontinued
0.6271	Remote Similarity	NPD5701	Approved
0.627	Remote Similarity	NPD6015	Approved
0.627	Remote Similarity	NPD6016	Approved
0.627	Remote Similarity	NPD6921	Approved
0.627	Remote Similarity	NPD5983	Phase 2
0.6262	Remote Similarity	NPD4249	Approved
0.625	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5369	Approved
0.6228	Remote Similarity	NPD7638	Approved
0.622	Remote Similarity	NPD5988	Approved
0.6218	Remote Similarity	NPD6011	Approved
0.6202	Remote Similarity	NPD8451	Approved
0.6202	Remote Similarity	NPD6336	Discontinued
0.619	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4270	Approved
0.619	Remote Similarity	NPD4269	Approved
0.6174	Remote Similarity	NPD7640	Approved
0.6174	Remote Similarity	NPD7639	Approved
0.6168	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD1694	Approved
0.6154	Remote Similarity	NPD8448	Approved
0.6154	Remote Similarity	NPD4820	Approved
0.6154	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4822	Approved
0.6154	Remote Similarity	NPD4819	Approved
0.6154	Remote Similarity	NPD4821	Approved
0.6142	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6412	Phase 2
0.6132	Remote Similarity	NPD5362	Discontinued
0.6106	Remote Similarity	NPD5695	Phase 3
0.6098	Remote Similarity	NPD8133	Approved
0.6091	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6101	Approved
0.608	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD2204	Approved
0.605	Remote Similarity	NPD6008	Approved
0.6038	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4756	Discovery
0.6016	Remote Similarity	NPD8266	Approved
0.6016	Remote Similarity	NPD8267	Approved
0.6016	Remote Similarity	NPD8268	Approved
0.6016	Remote Similarity	NPD8269	Approved
0.6015	Remote Similarity	NPD8392	Approved
0.6015	Remote Similarity	NPD8390	Approved
0.6015	Remote Similarity	NPD8391	Approved
0.6	Remote Similarity	NPD8341	Approved
0.6	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD8340	Approved
0.6	Remote Similarity	NPD8342	Approved
0.6	Remote Similarity	NPD8299	Approved
0.6	Remote Similarity	NPD4252	Approved
0.5984	Remote Similarity	NPD7101	Approved
0.5984	Remote Similarity	NPD7100	Approved
0.5984	Remote Similarity	NPD4634	Approved
0.5982	Remote Similarity	NPD6411	Approved
0.5966	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD5210	Approved
0.5965	Remote Similarity	NPD4629	Approved
0.5962	Remote Similarity	NPD4268	Approved
0.5962	Remote Similarity	NPD4271	Approved
0.5962	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD8415	Approved
0.5954	Remote Similarity	NPD8273	Phase 1
0.5938	Remote Similarity	NPD7909	Approved
0.5932	Remote Similarity	NPD5211	Phase 2
0.5929	Remote Similarity	NPD6399	Phase 3
0.5906	Remote Similarity	NPD7328	Approved
0.5906	Remote Similarity	NPD7327	Approved
0.5906	Remote Similarity	NPD6335	Approved
0.5897	Remote Similarity	NPD4696	Approved
0.5897	Remote Similarity	NPD5285	Approved
0.5897	Remote Similarity	NPD5286	Approved
0.5891	Remote Similarity	NPD8033	Approved
0.5891	Remote Similarity	NPD7503	Approved
0.5865	Remote Similarity	NPD6033	Approved
0.5862	Remote Similarity	NPD4755	Approved
0.5859	Remote Similarity	NPD7516	Approved
0.5856	Remote Similarity	NPD5737	Approved
0.5856	Remote Similarity	NPD6672	Approved
0.5841	Remote Similarity	NPD5693	Phase 1
0.5833	Remote Similarity	NPD5141	Approved
0.5827	Remote Similarity	NPD6317	Approved
0.5827	Remote Similarity	NPD7500	Approved
0.5827	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD7331	Phase 2
0.5814	Remote Similarity	NPD8294	Approved
0.5814	Remote Similarity	NPD8377	Approved
0.5814	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD5224	Approved
0.5798	Remote Similarity	NPD5225	Approved
0.5798	Remote Similarity	NPD5226	Approved
0.5798	Remote Similarity	NPD4633	Approved
0.5781	Remote Similarity	NPD6314	Approved
0.5781	Remote Similarity	NPD6313	Approved
0.578	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD3197	Phase 1
0.5772	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6908	Approved
0.5769	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD8380	Approved
0.5769	Remote Similarity	NPD8296	Approved
0.5769	Remote Similarity	NPD8379	Approved
0.5769	Remote Similarity	NPD6909	Approved
0.5769	Remote Similarity	NPD8378	Approved
0.5769	Remote Similarity	NPD8335	Approved
0.5763	Remote Similarity	NPD4700	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