NPASS Compound

Structure

NPC470753 OpenBabel07101718322D 40 43 0 0 1 0 0 0 0 0999 V2000 -3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 -3.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -3.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 -1.5000 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 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 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 -5.1962 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 2 0 0 0 0 2 27 1 0 0 0 0 3 34 1 0 0 0 0 4 34 1 0 0 0 0 5 35 1 0 0 0 0 6 35 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 17 1 0 0 0 0 11 18 2 0 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 14 23 1 0 0 0 0 15 27 2 0 0 0 0 16 26 1 0 0 0 0 17 28 2 0 0 0 0 18 28 1 0 0 0 0 19 32 1 0 0 0 0 20 24 1 0 0 0 0 20 31 1 0 0 0 0 21 34 1 0 0 0 0 22 35 1 0 0 0 0 23 36 1 0 0 0 0 24 37 1 0 0 0 0 26 29 1 0 0 0 0 27 30 1 0 0 0 0 28 33 1 0 0 0 0 29 25 1 1 0 0 0 29 34 1 0 0 0 0 30 25 1 6 0 0 0 30 40 1 0 0 0 0 31 35 1 0 0 0 0 31 36 1 1 0 0 0 32 36 1 1 0 0 0 32 37 1 0 0 0 0 33 38 2 0 0 0 0 33 40 1 0 0 0 0 36 7 1 1 0 0 0 37 8 1 1 0 0 0 37 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	548.42
Volume:	624.834
LogP:	8.623
LogD:	5.947
LogS:	-6.904
# Rotatable Bonds:	9
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.26
Synthetic Accessibility Score:	4.674
Fsp3:	0.703
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.743
MDCK Permeability:	1.2289596270420589e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.393
30% Bioavailability (F30%):	0.803

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	96.53790283203125%
Volume Distribution (VD):	1.744
Pgp-substrate:	2.2607154846191406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.288
CYP2C19-inhibitor:	0.175
CYP2C19-substrate:	0.775
CYP2C9-inhibitor:	0.162
CYP2C9-substrate:	0.827
CYP2D6-inhibitor:	0.326
CYP2D6-substrate:	0.478
CYP3A4-inhibitor:	0.622
CYP3A4-substrate:	0.387

ADMET: Excretion

Clearance (CL):	7.282
Half-life (T1/2):	0.005

ADMET: Toxicity

hERG Blockers:	0.429
Human Hepatotoxicity (H-HT):	0.076
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.378
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.586
Carcinogencity:	0.085
Eye Corrosion:	0.012
Eye Irritation:	0.438
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC470753

Natural Product ID:	NPC470753
*Common Name:**	(1R,2R,4As,8As,3'e,5's,1''s)-(+)-1-[6'-(2'',2''-Dimethyl-6''-Methylenecyclohexyl)-4'-Methyl-5'-Benzoyloxyhex-3'-Enyl]-2,5,5,8A-Tetramethyldecahydronaphthalen-2-Ol
IUPAC Name:	[(E,2S)-6-[(1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-1-[(1S)-2,2-dimethyl-6-methylidenecyclohexyl]-3-methylhex-3-en-2-yl] benzoate
Synonyms:
Standard InCHIKey:	PUPSZAFUUHIATB-OIUFFDPKSA-N
Standard InCHI:	InChI=1S/C37H56O3/c1-26-16-13-21-34(3,4)29(26)25-30(40-33(38)28-17-10-9-11-18-28)27(2)15-12-19-32-36(7)23-14-22-35(5,6)31(36)20-24-37(32,8)39/h9-11,15,17-18,29-32,39H,1,12-14,16,19-25H2,2-8H3/b27-15+/t29-,30+,31+,32-,36+,37-/m1/s1
SMILES:	CC(=CCCC1C2(CCCC(C2CCC1(C)O)(C)C)C)C(CC3C(=C)CCCC3(C)C)OC(=O)C4=CC=CC=C4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL221136
PubChem CID:	16109746
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO33073	physeter macrocephalus	Species	Physeteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17315955]

☑ 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	4
Others	1

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1183	Cell Line	WiDr	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[573868]
NPT81	Cell Line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[573868]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[573868]
NPT27	Others	Unspecified		ED50	>	10.0	ug ml-1	PMID[573868]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	115.5	%	PMID[573868]

☑ 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 NPC470753 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	267
0.1-0.2	1171
0.2-0.3	2003
0.3-0.4	4538
0.4-0.5	9625
0.5-0.6	14641
0.6-0.7	8770
0.7-0.8	1381
0.8-0.85	248
0.85-0.9	42
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473220
0.9916	High Similarity	NPC470765
0.9268	High Similarity	NPC275576
0.9194	High Similarity	NPC169913
0.9141	High Similarity	NPC203486
0.9141	High Similarity	NPC126516
0.9141	High Similarity	NPC329913
0.9141	High Similarity	NPC48929
0.8915	High Similarity	NPC472656
0.8872	High Similarity	NPC224491
0.8828	High Similarity	NPC147561
0.8815	High Similarity	NPC472569
0.8815	High Similarity	NPC25768
0.8815	High Similarity	NPC57628
0.8815	High Similarity	NPC188865
0.8815	High Similarity	NPC475122
0.8815	High Similarity	NPC95265
0.8815	High Similarity	NPC11685
0.8815	High Similarity	NPC95810
0.8815	High Similarity	NPC163719
0.8815	High Similarity	NPC472570
0.8815	High Similarity	NPC70716
0.8815	High Similarity	NPC125106
0.8815	High Similarity	NPC472573
0.8815	High Similarity	NPC476974
0.876	High Similarity	NPC470278
0.876	High Similarity	NPC72915
0.875	High Similarity	NPC472568
0.875	High Similarity	NPC473088
0.875	High Similarity	NPC171525
0.875	High Similarity	NPC174982
0.875	High Similarity	NPC470159
0.875	High Similarity	NPC472575
0.875	High Similarity	NPC29704
0.875	High Similarity	NPC472571
0.875	High Similarity	NPC476973
0.875	High Similarity	NPC184817
0.875	High Similarity	NPC470157
0.875	High Similarity	NPC469349
0.875	High Similarity	NPC177940
0.875	High Similarity	NPC472572
0.875	High Similarity	NPC471104
0.875	High Similarity	NPC70403
0.875	High Similarity	NPC158663
0.875	High Similarity	NPC200471
0.875	High Similarity	NPC472556
0.875	High Similarity	NPC96903
0.8741	High Similarity	NPC91703
0.8741	High Similarity	NPC163087
0.8741	High Similarity	NPC477468
0.8739	High Similarity	NPC128368
0.8731	High Similarity	NPC16912
0.8722	High Similarity	NPC214550
0.8722	High Similarity	NPC475652
0.8722	High Similarity	NPC210591
0.8712	High Similarity	NPC472374
0.8712	High Similarity	NPC472551
0.8712	High Similarity	NPC472545
0.8712	High Similarity	NPC472372
0.8689	High Similarity	NPC45794
0.8686	High Similarity	NPC473602
0.8676	High Similarity	NPC241951
0.8676	High Similarity	NPC470152
0.8676	High Similarity	NPC475759
0.8657	High Similarity	NPC473109
0.8657	High Similarity	NPC200592
0.8657	High Similarity	NPC48017
0.8657	High Similarity	NPC90614
0.8657	High Similarity	NPC100913
0.8657	High Similarity	NPC211137
0.8657	High Similarity	NPC4341
0.8657	High Similarity	NPC476094
0.8657	High Similarity	NPC184747
0.8657	High Similarity	NPC275592
0.8657	High Similarity	NPC473613
0.8657	High Similarity	NPC473112
0.8657	High Similarity	NPC473081
0.8657	High Similarity	NPC473060
0.8657	High Similarity	NPC43241
0.8657	High Similarity	NPC473758
0.8657	High Similarity	NPC147880
0.8657	High Similarity	NPC171207
0.8657	High Similarity	NPC473085
0.8657	High Similarity	NPC97667
0.8647	High Similarity	NPC183122
0.8647	High Similarity	NPC39549
0.8647	High Similarity	NPC283375
0.8647	High Similarity	NPC475373
0.8636	High Similarity	NPC477893
0.8636	High Similarity	NPC477896
0.8629	High Similarity	NPC473243
0.8623	High Similarity	NPC281717
0.8594	High Similarity	NPC190849
0.8594	High Similarity	NPC171007
0.8593	High Similarity	NPC97947
0.8593	High Similarity	NPC291599
0.8593	High Similarity	NPC41481
0.8593	High Similarity	NPC472576
0.8593	High Similarity	NPC87448
0.8593	High Similarity	NPC118080
0.8593	High Similarity	NPC27377
0.8571	High Similarity	NPC477874
0.8571	High Similarity	NPC173569
0.8561	High Similarity	NPC270590
0.8561	High Similarity	NPC474608
0.8561	High Similarity	NPC471101
0.8561	High Similarity	NPC473215
0.8561	High Similarity	NPC266265
0.8561	High Similarity	NPC476975
0.8561	High Similarity	NPC92293
0.8561	High Similarity	NPC301556
0.8551	High Similarity	NPC474935
0.8529	High Similarity	NPC472546
0.8529	High Similarity	NPC34012
0.8519	High Similarity	NPC472547
0.8507	High Similarity	NPC249817
0.85	High Similarity	NPC112216
0.85	High Similarity	NPC470245
0.85	High Similarity	NPC7095
0.85	High Similarity	NPC473214
0.8496	Intermediate Similarity	NPC195647
0.8496	Intermediate Similarity	NPC472577
0.8496	Intermediate Similarity	NPC66761
0.8496	Intermediate Similarity	NPC291638
0.8496	Intermediate Similarity	NPC17877
0.8467	Intermediate Similarity	NPC191082
0.8467	Intermediate Similarity	NPC475429
0.8467	Intermediate Similarity	NPC139067
0.8467	Intermediate Similarity	NPC177340
0.8467	Intermediate Similarity	NPC473673
0.8467	Intermediate Similarity	NPC270498
0.8467	Intermediate Similarity	NPC477894
0.8467	Intermediate Similarity	NPC147217
0.8467	Intermediate Similarity	NPC246480
0.8456	Intermediate Similarity	NPC266374
0.8444	Intermediate Similarity	NPC216940
0.8444	Intermediate Similarity	NPC472371
0.8444	Intermediate Similarity	NPC22676
0.8444	Intermediate Similarity	NPC198621
0.8444	Intermediate Similarity	NPC472395
0.8444	Intermediate Similarity	NPC475482
0.8443	Intermediate Similarity	NPC221275
0.844	Intermediate Similarity	NPC470153
0.8429	Intermediate Similarity	NPC60509
0.8429	Intermediate Similarity	NPC250046
0.8429	Intermediate Similarity	NPC81698
0.8413	Intermediate Similarity	NPC50872
0.8409	Intermediate Similarity	NPC472394
0.8406	Intermediate Similarity	NPC470231
0.8406	Intermediate Similarity	NPC51314
0.8406	Intermediate Similarity	NPC67777
0.8397	Intermediate Similarity	NPC475138
0.8394	Intermediate Similarity	NPC172311
0.8385	Intermediate Similarity	NPC51448
0.8385	Intermediate Similarity	NPC115797
0.8382	Intermediate Similarity	NPC248287
0.8382	Intermediate Similarity	NPC234548
0.838	Intermediate Similarity	NPC477905
0.8369	Intermediate Similarity	NPC198455
0.8369	Intermediate Similarity	NPC477483
0.8369	Intermediate Similarity	NPC325032
0.8369	Intermediate Similarity	NPC165260
0.8369	Intermediate Similarity	NPC31829
0.8369	Intermediate Similarity	NPC161239
0.8358	Intermediate Similarity	NPC473399
0.8358	Intermediate Similarity	NPC473216
0.8345	Intermediate Similarity	NPC127857
0.8322	Intermediate Similarity	NPC256142
0.8322	Intermediate Similarity	NPC472005
0.8322	Intermediate Similarity	NPC1173
0.8322	Intermediate Similarity	NPC304876
0.8322	Intermediate Similarity	NPC473414
0.8322	Intermediate Similarity	NPC249471
0.8322	Intermediate Similarity	NPC472022
0.8322	Intermediate Similarity	NPC158333
0.8322	Intermediate Similarity	NPC472657
0.8322	Intermediate Similarity	NPC265395
0.8322	Intermediate Similarity	NPC472658
0.8322	Intermediate Similarity	NPC472030
0.8322	Intermediate Similarity	NPC237549
0.8322	Intermediate Similarity	NPC242262
0.8322	Intermediate Similarity	NPC257213
0.8322	Intermediate Similarity	NPC77719
0.831	Intermediate Similarity	NPC279442
0.8308	Intermediate Similarity	NPC253681
0.8295	Intermediate Similarity	NPC295664
0.8293	Intermediate Similarity	NPC186933
0.8286	Intermediate Similarity	NPC48599
0.8286	Intermediate Similarity	NPC209592
0.8286	Intermediate Similarity	NPC475552
0.8273	Intermediate Similarity	NPC38696
0.8271	Intermediate Similarity	NPC238370
0.8264	Intermediate Similarity	NPC282239
0.8264	Intermediate Similarity	NPC112523
0.8264	Intermediate Similarity	NPC228204
0.8264	Intermediate Similarity	NPC26033
0.8264	Intermediate Similarity	NPC114410
0.8261	Intermediate Similarity	NPC472801
0.8261	Intermediate Similarity	NPC304110
0.8261	Intermediate Similarity	NPC192658

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 NPC470753 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	824
0.2-0.3	1201
0.3-0.4	2486
0.4-0.5	2428
0.5-0.6	1490
0.6-0.7	440
0.7-0.8	44
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8538	High Similarity	NPD7008	Discontinued
0.8478	Intermediate Similarity	NPD7236	Approved
0.8258	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7239	Suspended
0.8145	Intermediate Similarity	NPD5951	Approved
0.8042	Intermediate Similarity	NPD6273	Approved
0.8	Intermediate Similarity	NPD7961	Discontinued
0.7967	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD8166	Discontinued
0.7943	Intermediate Similarity	NPD7003	Approved
0.7907	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2629	Approved
0.7857	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7610	Discontinued
0.7805	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD4198	Discontinued
0.7769	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD7094	Approved
0.7698	Intermediate Similarity	NPD6858	Approved
0.7682	Intermediate Similarity	NPD7057	Phase 3
0.7682	Intermediate Similarity	NPD7058	Phase 2
0.7661	Intermediate Similarity	NPD2182	Approved
0.7635	Intermediate Similarity	NPD7458	Discontinued
0.7609	Intermediate Similarity	NPD6663	Approved
0.7583	Intermediate Similarity	NPD1238	Approved
0.7574	Intermediate Similarity	NPD5736	Approved
0.7541	Intermediate Similarity	NPD1929	Approved
0.7541	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD1930	Approved
0.7519	Intermediate Similarity	NPD6287	Discontinued
0.7482	Intermediate Similarity	NPD7713	Phase 3
0.7468	Intermediate Similarity	NPD7799	Discontinued
0.7438	Intermediate Similarity	NPD2066	Phase 3
0.741	Intermediate Similarity	NPD3764	Approved
0.74	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD8127	Discontinued
0.7357	Intermediate Similarity	NPD8032	Phase 2
0.7357	Intermediate Similarity	NPD7715	Approved
0.7357	Intermediate Similarity	NPD7714	Approved
0.7348	Intermediate Similarity	NPD7741	Discontinued
0.7344	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD164	Approved
0.7339	Intermediate Similarity	NPD5909	Discontinued
0.7329	Intermediate Similarity	NPD4628	Phase 3
0.7312	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2346	Discontinued
0.7226	Intermediate Similarity	NPD1283	Approved
0.7222	Intermediate Similarity	NPD2799	Discontinued
0.72	Intermediate Similarity	NPD1237	Approved
0.7183	Intermediate Similarity	NPD4140	Approved
0.7172	Intermediate Similarity	NPD5408	Approved
0.7172	Intermediate Similarity	NPD5406	Approved
0.7172	Intermediate Similarity	NPD5404	Approved
0.7172	Intermediate Similarity	NPD5405	Approved
0.7143	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD2798	Approved
0.712	Intermediate Similarity	NPD6647	Phase 2
0.7115	Intermediate Similarity	NPD7768	Phase 2
0.7111	Intermediate Similarity	NPD3019	Approved
0.7099	Intermediate Similarity	NPD6010	Discontinued
0.7097	Intermediate Similarity	NPD7819	Suspended
0.7095	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD9545	Approved
0.709	Intermediate Similarity	NPD7009	Phase 2
0.7083	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1088	Approved
0.708	Intermediate Similarity	NPD3972	Approved
0.7073	Intermediate Similarity	NPD8368	Discontinued
0.7066	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2935	Discontinued
0.705	Intermediate Similarity	NPD2797	Approved
0.7049	Intermediate Similarity	NPD1989	Approved
0.7045	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD2313	Discontinued
0.704	Intermediate Similarity	NPD1932	Approved
0.7034	Intermediate Similarity	NPD7097	Phase 1
0.702	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7997	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6355	Discontinued
0.7007	Intermediate Similarity	NPD4807	Approved
0.7007	Intermediate Similarity	NPD4806	Approved
0.7007	Intermediate Similarity	NPD1281	Approved
0.6986	Remote Similarity	NPD4308	Phase 3
0.6985	Remote Similarity	NPD5306	Approved
0.6985	Remote Similarity	NPD2932	Approved
0.6985	Remote Similarity	NPD5305	Approved
0.6982	Remote Similarity	NPD8361	Approved
0.6982	Remote Similarity	NPD8360	Approved
0.6982	Remote Similarity	NPD8435	Approved
0.6977	Remote Similarity	NPD2329	Discontinued
0.6972	Remote Similarity	NPD7095	Approved
0.6957	Remote Similarity	NPD4878	Approved
0.6948	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD8407	Phase 2
0.6944	Remote Similarity	NPD2979	Phase 3
0.694	Remote Similarity	NPD9493	Approved
0.6923	Remote Similarity	NPD6798	Discontinued
0.6917	Remote Similarity	NPD1086	Approved
0.6917	Remote Similarity	NPD1090	Approved
0.6917	Remote Similarity	NPD9256	Approved
0.6917	Remote Similarity	NPD9258	Approved
0.6917	Remote Similarity	NPD1089	Approved
0.6912	Remote Similarity	NPD5691	Approved
0.6901	Remote Similarity	NPD6832	Phase 2
0.6885	Remote Similarity	NPD1202	Approved
0.6885	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD1201	Approved
0.688	Remote Similarity	NPD7798	Approved
0.6879	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6085	Phase 2
0.6871	Remote Similarity	NPD7305	Phase 1
0.6867	Remote Similarity	NPD4110	Phase 3
0.6867	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3750	Approved
0.6864	Remote Similarity	NPD8434	Phase 2
0.6861	Remote Similarity	NPD4626	Approved
0.6857	Remote Similarity	NPD1876	Approved
0.6857	Remote Similarity	NPD2199	Approved
0.6857	Remote Similarity	NPD5667	Approved
0.6857	Remote Similarity	NPD2198	Approved
0.6855	Remote Similarity	NPD3495	Discontinued
0.6853	Remote Similarity	NPD6966	Discovery
0.6853	Remote Similarity	NPD6039	Approved
0.6842	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3226	Approved
0.6839	Remote Similarity	NPD8485	Approved
0.6835	Remote Similarity	NPD1608	Approved
0.6835	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD800	Approved
0.6829	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1693	Approved
0.6828	Remote Similarity	NPD4307	Phase 2
0.6824	Remote Similarity	NPD4476	Approved
0.6824	Remote Similarity	NPD4477	Approved
0.6824	Remote Similarity	NPD2438	Suspended
0.6812	Remote Similarity	NPD3026	Approved
0.6812	Remote Similarity	NPD4136	Approved
0.6812	Remote Similarity	NPD3023	Approved
0.6812	Remote Similarity	NPD4106	Approved
0.6812	Remote Similarity	NPD4135	Approved
0.6809	Remote Similarity	NPD1470	Approved
0.6806	Remote Similarity	NPD3268	Approved
0.68	Remote Similarity	NPD9495	Approved
0.6794	Remote Similarity	NPD2067	Discontinued
0.6788	Remote Similarity	NPD5844	Phase 1
0.6788	Remote Similarity	NPD5585	Approved
0.6788	Remote Similarity	NPD3024	Approved
0.6788	Remote Similarity	NPD3025	Approved
0.6788	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5327	Phase 3
0.6786	Remote Similarity	NPD8313	Approved
0.6786	Remote Similarity	NPD8312	Approved
0.6783	Remote Similarity	NPD7055	Discontinued
0.6772	Remote Similarity	NPD5761	Phase 2
0.6772	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5760	Phase 2
0.6765	Remote Similarity	NPD8150	Discontinued
0.6763	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3748	Approved
0.6752	Remote Similarity	NPD6677	Suspended
0.6752	Remote Similarity	NPD7411	Suspended
0.675	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7748	Approved
0.6739	Remote Similarity	NPD1778	Approved
0.6735	Remote Similarity	NPD6353	Approved
0.673	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7177	Discontinued
0.6723	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD9257	Approved
0.6723	Remote Similarity	NPD9259	Approved
0.6721	Remote Similarity	NPD1239	Approved
0.672	Remote Similarity	NPD1564	Approved
0.672	Remote Similarity	NPD1565	Approved
0.672	Remote Similarity	NPD1566	Phase 3
0.6715	Remote Similarity	NPD1894	Discontinued
0.6715	Remote Similarity	NPD3091	Approved
0.6714	Remote Similarity	NPD6637	Approved
0.6712	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD5121	Approved
0.6712	Remote Similarity	NPD5120	Approved
0.6712	Remote Similarity	NPD5119	Approved
0.6711	Remote Similarity	NPD6099	Approved
0.6711	Remote Similarity	NPD2531	Phase 2
0.6711	Remote Similarity	NPD6100	Approved
0.671	Remote Similarity	NPD7427	Discontinued
0.6707	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD4879	Approved
0.669	Remote Similarity	NPD1164	Approved
0.6688	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6599	Discontinued
0.6688	Remote Similarity	NPD7028	Phase 2
0.6686	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4102	Approved
0.6667	Remote Similarity	NPD5157	Phase 1

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