NPASS Compound

Structure

CID243577 OpenBabel06191716042D 24 26 0 0 1 0 0 0 0 0999 V2000 -0.8340 1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4648 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9833 0.3525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6679 -1.9259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4286 -2.1095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0606 -1.5793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5019 -1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 -1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4985 -1.8603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4978 -0.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9589 -0.4775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9630 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1095 -1.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 1.4444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6679 0.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6679 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5019 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 -0.4815 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8340 2.4074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5019 1.4444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7640 0.5862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8169 -0.0403 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 14 1 0 0 0 0 7 11 2 0 0 0 0 7 14 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 24 1 0 0 0 0 12 14 2 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 20 1 6 0 0 0 15 16 1 0 0 0 0 15 21 1 1 0 0 0 16 17 1 0 0 0 0 16 22 2 0 0 0 0 17 18 1 0 0 0 0 17 19 1 1 0 0 0 19 20 1 6 0 0 0 20 23 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.21
Volume:	356.058
LogP:	3.472
LogD:	1.893
LogS:	-3.403
# Rotatable Bonds:	3
TPSA:	70.67
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.889
Synthetic Accessibility Score:	4.561
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.661
MDCK Permeability:	2.5849929443211295e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.037

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.786
Plasma Protein Binding (PPB):	94.14075469970703%
Volume Distribution (VD):	1.716
Pgp-substrate:	6.566925525665283%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.24
CYP2C19-inhibitor:	0.233
CYP2C19-substrate:	0.671
CYP2C9-inhibitor:	0.614
CYP2C9-substrate:	0.415
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.407
CYP3A4-inhibitor:	0.262
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	10.142
Half-life (T1/2):	0.275

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.274
Drug-inuced Liver Injury (DILI):	0.399
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.932
Maximum Recommended Daily Dose:	0.23
Skin Sensitization:	0.23
Carcinogencity:	0.763
Eye Corrosion:	0.006
Eye Irritation:	0.029
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC243577

Natural Product ID:	NPC243577
*Common Name:**	Leoheterin
IUPAC Name:	(2R,3R,4R,4aS,8aS)-4-[2-(furan-3-yl)ethyl]-2,4-dihydroxy-3,4a,8,8-tetramethyl-2,3,5,6,7,8a-hexahydronaphthalen-1-one
Synonyms:
Standard InCHIKey:	PVHCSUICRAIGCK-YJLWDSPXSA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-13-15(21)16(22)17-18(2,3)8-5-9-19(17,4)20(13,23)10-6-14-7-11-24-12-14/h7,11-13,15,17,21,23H,5-6,8-10H2,1-4H3/t13-,15-,17+,19+,20-/m1/s1
SMILES:	C[C@@H]1[C@H](C(=O)[C@H]2C(C)(C)CCC[C@]2(C)[C@]1(CCc1ccoc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3234610
PubChem CID:	15726751
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO23548	Leonurus heterophyllus	Species	Lamiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[22703163]
NPO23548	Leonurus heterophyllus	Species	Lamiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[24328283]
NPO23548	Leonurus heterophyllus	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[24704554]
NPO17287	Lagopsis supina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24707938]
NPO23548	Leonurus heterophyllus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32935986]
NPO23548	Leonurus heterophyllus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23548	Leonurus heterophyllus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23548	Leonurus heterophyllus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23548	Leonurus heterophyllus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17287	Lagopsis supina	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[545486]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	<	50.0	%	PMID[545485]

☑ 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 NPC243577 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	325
0.1-0.2	1294
0.2-0.3	2761
0.3-0.4	5617
0.4-0.5	11209
0.5-0.6	9651
0.6-0.7	9233
0.7-0.8	2179
0.8-0.85	298
0.85-0.9	111
0.9-0.95	17
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9348	High Similarity	NPC67003
0.9291	High Similarity	NPC5676
0.9197	High Similarity	NPC46896
0.9085	High Similarity	NPC251865
0.9078	High Similarity	NPC121158
0.9071	High Similarity	NPC90296
0.9065	High Similarity	NPC471996
0.9034	High Similarity	NPC125182
0.9034	High Similarity	NPC69647
0.9028	High Similarity	NPC255414
0.8993	High Similarity	NPC249021
0.8986	High Similarity	NPC158525
0.8973	High Similarity	NPC212257
0.8944	High Similarity	NPC263337
0.8933	High Similarity	NPC475967
0.8904	High Similarity	NPC195325
0.8904	High Similarity	NPC472654
0.8897	High Similarity	NPC471174
0.8897	High Similarity	NPC216755
0.8867	High Similarity	NPC304692
0.8867	High Similarity	NPC472772
0.8851	High Similarity	NPC469503
0.8851	High Similarity	NPC246164
0.8851	High Similarity	NPC75906
0.8851	High Similarity	NPC268905
0.8849	High Similarity	NPC476947
0.8832	High Similarity	NPC61788
0.8816	High Similarity	NPC82851
0.8816	High Similarity	NPC5079
0.8811	High Similarity	NPC52412
0.88	High Similarity	NPC104736
0.88	High Similarity	NPC41880
0.8792	High Similarity	NPC282445
0.8792	High Similarity	NPC178932
0.8784	High Similarity	NPC272590
0.8776	High Similarity	NPC211625
0.8776	High Similarity	NPC470998
0.8768	High Similarity	NPC471995
0.8759	High Similarity	NPC185456
0.8758	High Similarity	NPC234660
0.8758	High Similarity	NPC39986
0.8758	High Similarity	NPC51568
0.8758	High Similarity	NPC302369
0.8758	High Similarity	NPC477405
0.8758	High Similarity	NPC134254
0.875	High Similarity	NPC335761
0.875	High Similarity	NPC476946
0.8742	High Similarity	NPC261597
0.8742	High Similarity	NPC194499
0.8733	High Similarity	NPC44675
0.8733	High Similarity	NPC75310
0.8733	High Similarity	NPC214541
0.8733	High Similarity	NPC35000
0.8733	High Similarity	NPC469336
0.8723	High Similarity	NPC4764
0.8716	High Similarity	NPC196846
0.871	High Similarity	NPC472774
0.871	High Similarity	NPC472775
0.8705	High Similarity	NPC218838
0.8701	High Similarity	NPC476857
0.8701	High Similarity	NPC476856
0.8701	High Similarity	NPC276551
0.8701	High Similarity	NPC476858
0.8693	High Similarity	NPC472771
0.8693	High Similarity	NPC329938
0.8693	High Similarity	NPC69028
0.8693	High Similarity	NPC18986
0.869	High Similarity	NPC476944
0.8684	High Similarity	NPC474611
0.8684	High Similarity	NPC140952
0.8667	High Similarity	NPC114880
0.8667	High Similarity	NPC57998
0.8667	High Similarity	NPC30222
0.8654	High Similarity	NPC471397
0.8645	High Similarity	NPC23387
0.8645	High Similarity	NPC470875
0.8639	High Similarity	NPC302987
0.8639	High Similarity	NPC221809
0.8636	High Similarity	NPC663
0.8636	High Similarity	NPC283209
0.8636	High Similarity	NPC292389
0.8636	High Similarity	NPC224394
0.8636	High Similarity	NPC469338
0.8636	High Similarity	NPC472773
0.8627	High Similarity	NPC470789
0.8627	High Similarity	NPC25255
0.8627	High Similarity	NPC472653
0.8627	High Similarity	NPC477402
0.8621	High Similarity	NPC64568
0.8618	High Similarity	NPC45101
0.8618	High Similarity	NPC81405
0.8618	High Similarity	NPC195954
0.8618	High Similarity	NPC88007
0.8618	High Similarity	NPC187149
0.8618	High Similarity	NPC36655
0.8618	High Similarity	NPC299038
0.8609	High Similarity	NPC141538
0.8609	High Similarity	NPC155939
0.8609	High Similarity	NPC92979
0.8609	High Similarity	NPC296807
0.8601	High Similarity	NPC90953
0.86	High Similarity	NPC470996
0.86	High Similarity	NPC294511
0.86	High Similarity	NPC121615
0.86	High Similarity	NPC475777
0.8599	High Similarity	NPC470995
0.8591	High Similarity	NPC477404
0.8591	High Similarity	NPC470997
0.8591	High Similarity	NPC476122
0.8591	High Similarity	NPC196864
0.8591	High Similarity	NPC156189
0.8591	High Similarity	NPC228842
0.859	High Similarity	NPC476850
0.859	High Similarity	NPC476853
0.859	High Similarity	NPC472282
0.859	High Similarity	NPC173516
0.859	High Similarity	NPC476861
0.8581	High Similarity	NPC469849
0.8581	High Similarity	NPC476860
0.8581	High Similarity	NPC271657
0.8581	High Similarity	NPC470940
0.8581	High Similarity	NPC123088
0.8571	High Similarity	NPC470999
0.8571	High Similarity	NPC97904
0.8571	High Similarity	NPC117986
0.8571	High Similarity	NPC200782
0.8571	High Similarity	NPC68848
0.8571	High Similarity	NPC263432
0.8571	High Similarity	NPC193798
0.8571	High Similarity	NPC18347
0.8571	High Similarity	NPC79571
0.8571	High Similarity	NPC149896
0.8562	High Similarity	NPC477403
0.8562	High Similarity	NPC475226
0.8561	High Similarity	NPC89133
0.8553	High Similarity	NPC209364
0.8553	High Similarity	NPC107646
0.8552	High Similarity	NPC473152
0.8552	High Similarity	NPC62103
0.8552	High Similarity	NPC20578
0.8535	High Similarity	NPC160651
0.8535	High Similarity	NPC271235
0.8526	High Similarity	NPC121995
0.8523	High Similarity	NPC234494
0.8516	High Similarity	NPC285567
0.8514	High Similarity	NPC286038
0.8514	High Similarity	NPC250228
0.8506	High Similarity	NPC8389
0.8503	High Similarity	NPC41182
0.8497	Intermediate Similarity	NPC214495
0.8497	Intermediate Similarity	NPC475066
0.8497	Intermediate Similarity	NPC470119
0.8497	Intermediate Similarity	NPC286722
0.8497	Intermediate Similarity	NPC470118
0.8493	Intermediate Similarity	NPC103134
0.8487	Intermediate Similarity	NPC264943
0.8483	Intermediate Similarity	NPC205765
0.8477	Intermediate Similarity	NPC476201
0.8477	Intermediate Similarity	NPC472672
0.8477	Intermediate Similarity	NPC33938
0.8471	Intermediate Similarity	NPC472651
0.8467	Intermediate Similarity	NPC469335
0.8467	Intermediate Similarity	NPC23086
0.8467	Intermediate Similarity	NPC159927
0.8456	Intermediate Similarity	NPC471007
0.8456	Intermediate Similarity	NPC66991
0.8456	Intermediate Similarity	NPC19747
0.8452	Intermediate Similarity	NPC470792
0.8452	Intermediate Similarity	NPC472767
0.8452	Intermediate Similarity	NPC470939
0.8452	Intermediate Similarity	NPC96443
0.8452	Intermediate Similarity	NPC290400
0.8452	Intermediate Similarity	NPC188649
0.8446	Intermediate Similarity	NPC262198
0.8446	Intermediate Similarity	NPC346
0.8446	Intermediate Similarity	NPC62799
0.8442	Intermediate Similarity	NPC472823
0.8442	Intermediate Similarity	NPC475295
0.8442	Intermediate Similarity	NPC472671
0.8442	Intermediate Similarity	NPC473473
0.8442	Intermediate Similarity	NPC307383
0.8431	Intermediate Similarity	NPC60973
0.8431	Intermediate Similarity	NPC263265
0.8431	Intermediate Similarity	NPC469485
0.8431	Intermediate Similarity	NPC126723
0.8428	Intermediate Similarity	NPC285227
0.8421	Intermediate Similarity	NPC98206
0.8421	Intermediate Similarity	NPC302054
0.8421	Intermediate Similarity	NPC253201
0.8421	Intermediate Similarity	NPC34421
0.8421	Intermediate Similarity	NPC237259
0.8418	Intermediate Similarity	NPC472652
0.8414	Intermediate Similarity	NPC56197
0.8411	Intermediate Similarity	NPC18135
0.8408	Intermediate Similarity	NPC478178
0.8408	Intermediate Similarity	NPC214600
0.8408	Intermediate Similarity	NPC149945
0.8403	Intermediate Similarity	NPC476943
0.84	Intermediate Similarity	NPC470790
0.84	Intermediate Similarity	NPC470791

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 NPC243577 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	923
0.2-0.3	1884
0.3-0.4	2668
0.4-0.5	2009
0.5-0.6	1016
0.6-0.7	324
0.7-0.8	26
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8733	High Similarity	NPD5760	Phase 2
0.8733	High Similarity	NPD5761	Phase 2
0.8133	Intermediate Similarity	NPD8434	Phase 2
0.7831	Intermediate Similarity	NPD6764	Approved
0.7831	Intermediate Similarity	NPD6765	Approved
0.7697	Intermediate Similarity	NPD4628	Phase 3
0.7647	Intermediate Similarity	NPD6785	Approved
0.7647	Intermediate Similarity	NPD6784	Approved
0.7616	Intermediate Similarity	NPD1471	Phase 3
0.75	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6599	Discontinued
0.7389	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD3882	Suspended
0.7346	Intermediate Similarity	NPD7819	Suspended
0.7346	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6273	Approved
0.732	Intermediate Similarity	NPD6099	Approved
0.732	Intermediate Similarity	NPD2796	Approved
0.732	Intermediate Similarity	NPD6100	Approved
0.7296	Intermediate Similarity	NPD920	Approved
0.729	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2344	Approved
0.7229	Intermediate Similarity	NPD5494	Approved
0.7226	Intermediate Similarity	NPD1549	Phase 2
0.7215	Intermediate Similarity	NPD6799	Approved
0.7212	Intermediate Similarity	NPD3749	Approved
0.7212	Intermediate Similarity	NPD7075	Discontinued
0.7209	Intermediate Similarity	NPD6559	Discontinued
0.7195	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1247	Approved
0.7179	Intermediate Similarity	NPD2800	Approved
0.7178	Intermediate Similarity	NPD6801	Discontinued
0.717	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD919	Approved
0.7161	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7236	Approved
0.7143	Intermediate Similarity	NPD2799	Discontinued
0.7134	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD3972	Approved
0.7101	Intermediate Similarity	NPD3926	Phase 2
0.7089	Intermediate Similarity	NPD2309	Approved
0.7063	Intermediate Similarity	NPD2532	Approved
0.7063	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2533	Approved
0.7063	Intermediate Similarity	NPD2534	Approved
0.7055	Intermediate Similarity	NPD4380	Phase 2
0.7045	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD5844	Phase 1
0.7032	Intermediate Similarity	NPD1510	Phase 2
0.7031	Intermediate Similarity	NPD8404	Phase 2
0.7025	Intermediate Similarity	NPD3750	Approved
0.7013	Intermediate Similarity	NPD1607	Approved
0.7012	Intermediate Similarity	NPD7411	Suspended
0.7007	Intermediate Similarity	NPD1608	Approved
0.6994	Remote Similarity	NPD3226	Approved
0.6994	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1240	Approved
0.6987	Remote Similarity	NPD1551	Phase 2
0.6982	Remote Similarity	NPD6959	Discontinued
0.6977	Remote Similarity	NPD3818	Discontinued
0.6974	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1934	Approved
0.6962	Remote Similarity	NPD1243	Approved
0.6959	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6166	Phase 2
0.6948	Remote Similarity	NPD6355	Discontinued
0.6943	Remote Similarity	NPD2346	Discontinued
0.6933	Remote Similarity	NPD7239	Suspended
0.6923	Remote Similarity	NPD3748	Approved
0.6923	Remote Similarity	NPD7033	Discontinued
0.6905	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD970	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7458	Discontinued
0.6886	Remote Similarity	NPD5402	Approved
0.6886	Remote Similarity	NPD3817	Phase 2
0.6886	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD8127	Discontinued
0.6879	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD5403	Approved
0.6863	Remote Similarity	NPD3764	Approved
0.6852	Remote Similarity	NPD5401	Approved
0.6851	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5762	Approved
0.6835	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6004	Phase 3
0.6835	Remote Similarity	NPD6005	Phase 3
0.6835	Remote Similarity	NPD5763	Approved
0.6835	Remote Similarity	NPD6002	Phase 3
0.6835	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD2801	Approved
0.6813	Remote Similarity	NPD7003	Approved
0.681	Remote Similarity	NPD1512	Approved
0.6803	Remote Similarity	NPD17	Approved
0.6803	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1876	Approved
0.6791	Remote Similarity	NPD3057	Approved
0.6782	Remote Similarity	NPD3751	Discontinued
0.678	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4140	Approved
0.677	Remote Similarity	NPD3887	Approved
0.6766	Remote Similarity	NPD37	Approved
0.6763	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD2313	Discontinued
0.6753	Remote Similarity	NPD3268	Approved
0.6746	Remote Similarity	NPD4967	Phase 2
0.6746	Remote Similarity	NPD7768	Phase 2
0.6746	Remote Similarity	NPD4965	Approved
0.6746	Remote Similarity	NPD4966	Approved
0.6744	Remote Similarity	NPD3787	Discontinued
0.6744	Remote Similarity	NPD7229	Phase 3
0.6724	Remote Similarity	NPD7473	Discontinued
0.6711	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD2798	Approved
0.671	Remote Similarity	NPD8032	Phase 2
0.6709	Remote Similarity	NPD4308	Phase 3
0.6708	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD4110	Phase 3
0.6705	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD3533	Approved
0.6702	Remote Similarity	NPD2972	Approved
0.6689	Remote Similarity	NPD1778	Approved
0.6688	Remote Similarity	NPD6651	Approved
0.6687	Remote Similarity	NPD2424	Discontinued
0.6687	Remote Similarity	NPD1511	Approved
0.6686	Remote Similarity	NPD7199	Phase 2
0.6686	Remote Similarity	NPD7799	Discontinued
0.6686	Remote Similarity	NPD2163	Approved
0.6667	Remote Similarity	NPD6280	Approved
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD6797	Phase 2
0.6667	Remote Similarity	NPD6279	Approved
0.6667	Remote Similarity	NPD1241	Discontinued
0.6667	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2354	Approved
0.6648	Remote Similarity	NPD8313	Approved
0.6648	Remote Similarity	NPD8312	Approved
0.6647	Remote Similarity	NPD7057	Phase 3
0.6647	Remote Similarity	NPD7058	Phase 2
0.6647	Remote Similarity	NPD6808	Phase 2
0.6647	Remote Similarity	NPD6232	Discontinued
0.6645	Remote Similarity	NPD2797	Approved
0.6645	Remote Similarity	NPD6798	Discontinued
0.6629	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7251	Discontinued
0.6624	Remote Similarity	NPD5735	Approved
0.6623	Remote Similarity	NPD6832	Phase 2
0.6616	Remote Similarity	NPD4111	Phase 1
0.6616	Remote Similarity	NPD4665	Approved
0.6614	Remote Similarity	NPD2491	Approved
0.6613	Remote Similarity	NPD2974	Approved
0.6613	Remote Similarity	NPD2975	Approved
0.6613	Remote Similarity	NPD2973	Approved
0.6611	Remote Similarity	NPD8407	Phase 2
0.661	Remote Similarity	NPD7074	Phase 3
0.6601	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD9092	Discovery
0.6596	Remote Similarity	NPD6782	Approved
0.6596	Remote Similarity	NPD6780	Approved
0.6596	Remote Similarity	NPD6776	Approved
0.6596	Remote Similarity	NPD6779	Approved
0.6596	Remote Similarity	NPD6781	Approved
0.6596	Remote Similarity	NPD6778	Approved
0.6596	Remote Similarity	NPD6777	Approved
0.6596	Remote Similarity	NPD4107	Approved
0.6596	Remote Similarity	NPD4580	Approved
0.6592	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD7808	Phase 3
0.6591	Remote Similarity	NPD7177	Discontinued
0.6588	Remote Similarity	NPD2296	Approved
0.6587	Remote Similarity	NPD2649	Approved
0.6587	Remote Similarity	NPD2651	Approved
0.6585	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7095	Approved
0.6579	Remote Similarity	NPD1283	Approved
0.6573	Remote Similarity	NPD5953	Discontinued
0.6571	Remote Similarity	NPD2403	Approved
0.657	Remote Similarity	NPD6234	Discontinued
0.6564	Remote Similarity	NPD6190	Approved
0.6561	Remote Similarity	NPD4307	Phase 2
0.6561	Remote Similarity	NPD4060	Phase 1
0.6558	Remote Similarity	NPD9494	Approved
0.6554	Remote Similarity	NPD9545	Approved
0.6554	Remote Similarity	NPD7054	Approved
0.6552	Remote Similarity	NPD5710	Approved
0.6552	Remote Similarity	NPD5711	Approved
0.6548	Remote Similarity	NPD7028	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data