NPASS Compound

Structure

NPC475456 OpenBabel07101718182D 39 43 0 0 1 0 0 0 0 0999 V2000 0.2788 1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3685 -1.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7350 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2350 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7350 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2709 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6994 -1.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8690 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1369 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7350 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2709 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6728 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0084 -2.9190 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 2.4049 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 29 1 0 0 0 0 6 29 1 0 0 0 0 7 30 1 0 0 0 0 8 31 1 0 0 0 0 9 32 1 0 0 0 0 10 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 12 29 1 0 0 0 0 13 30 1 0 0 0 0 14 31 1 0 0 0 0 15 21 1 0 0 0 0 15 24 1 0 0 0 0 16 23 1 0 0 0 0 16 25 1 0 0 0 0 17 1 1 1 0 0 0 17 26 1 0 0 0 0 17 36 1 0 0 0 0 18 33 2 0 0 0 0 18 37 1 0 0 0 0 19 34 2 0 0 0 0 19 38 1 0 0 0 0 20 35 2 0 0 0 0 20 39 1 0 0 0 0 21 26 1 0 0 0 0 21 37 1 1 0 0 0 22 29 1 0 0 0 0 22 30 1 1 0 0 0 23 30 1 1 0 0 0 23 31 1 0 0 0 0 24 31 1 1 0 0 0 24 32 1 0 0 0 0 25 32 1 6 0 0 0 25 38 1 0 0 0 0 26 27 1 0 0 0 0 27 28 1 0 0 0 0 27 32 1 0 0 0 0 28 36 1 0 0 0 0 28 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	546.36
Volume:	572.868
LogP:	5.563
LogD:	4.089
LogS:	-5.344
# Rotatable Bonds:	6
TPSA:	88.13
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.314
Synthetic Accessibility Score:	5.205
Fsp3:	0.906
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-4.77
MDCK Permeability:	5.0997019570786506e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.031
30% Bioavailability (F30%):	0.884

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.299
Plasma Protein Binding (PPB):	77.42914581298828%
Volume Distribution (VD):	1.85
Pgp-substrate:	21.671253204345703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.069
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.698
CYP2C9-inhibitor:	0.101
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.059
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.395
CYP3A4-substrate:	0.293

ADMET: Excretion

Clearance (CL):	3.253
Half-life (T1/2):	0.143

ADMET: Toxicity

hERG Blockers:	0.738
Human Hepatotoxicity (H-HT):	0.217
Drug-inuced Liver Injury (DILI):	0.882
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.73
Maximum Recommended Daily Dose:	0.041
Skin Sensitization:	0.828
Carcinogencity:	0.144
Eye Corrosion:	0.866
Eye Irritation:	0.039
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC475456

Natural Product ID:	NPC475456
*Common Name:**	(1S,3S,3Ar,4S,5As,5Br,7As,11As,11Br,13S,13As,13Bs)-3,5B,8,8,11A,13A-Hexamethylicosahydrochryseno[2,1-C]Furan-1,4,13-Triyl Triacetate
IUPAC Name:	[(1S,3S,3aR,4S,5aS,5bR,7aS,11aS,11bR,13S,13aS,13bS)-1,13-diacetyloxy-3,5b,8,8,11a,13a-hexamethyl-1,3,3a,4,5,5a,6,7,7a,9,10,11,11b,12,13,13b-hexadecahydrophenanthro[2,1-e][2]benzofuran-4-yl] acetate
Synonyms:
Standard InCHIKey:	WDIUWWFQJBCYNO-VVKPQIAZSA-N
Standard InCHI:	InChI=1S/C32H50O7/c1-17-26-21(37-18(2)33)15-24-31(8)14-11-22-29(5,6)12-10-13-30(22,7)23(31)16-25(38-19(3)34)32(24,9)27(26)28(36-17)39-20(4)35/h17,21-28H,10-16H2,1-9H3/t17-,21-,22-,23+,24-,25-,26+,27+,28-,30-,31+,32+/m0/s1
SMILES:	CC(=O)O[C@H]1C[C@H]2[C@@]([C@H]3[C@@]1(C)[C@H]1[C@H](OC(=O)C)O[C@H]([C@@H]1[C@H](C3)OC(=O)C)C)(C)CC[C@@H]1[C@]2(C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505997
PubChem CID:	11038884
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

*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
NPO33404	phyllospongia sp.	Species	Thorectidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[12502324]

☑ 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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	Inhibition	=	30.0	%	PMID[465043]

☑ 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 NPC475456 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	470
0.1-0.2	4578
0.2-0.3	13612
0.3-0.4	10812
0.4-0.5	5429
0.5-0.6	3793
0.6-0.7	3208
0.7-0.8	721
0.8-0.85	63
0.85-0.9	3
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9359	High Similarity	NPC474284
0.9359	High Similarity	NPC475820
0.9359	High Similarity	NPC213737
0.9359	High Similarity	NPC474253
0.9359	High Similarity	NPC474346
0.9231	High Similarity	NPC2096
0.9231	High Similarity	NPC208912
0.8734	High Similarity	NPC471216
0.8734	High Similarity	NPC471217
0.8625	High Similarity	NPC71541
0.8333	Intermediate Similarity	NPC471411
0.8333	Intermediate Similarity	NPC471410
0.8214	Intermediate Similarity	NPC235402
0.8171	Intermediate Similarity	NPC476494
0.8171	Intermediate Similarity	NPC73515
0.8148	Intermediate Similarity	NPC477287
0.8132	Intermediate Similarity	NPC209798
0.8132	Intermediate Similarity	NPC471374
0.8132	Intermediate Similarity	NPC471375
0.8118	Intermediate Similarity	NPC474008
0.8111	Intermediate Similarity	NPC238796
0.8111	Intermediate Similarity	NPC203434
0.8111	Intermediate Similarity	NPC237071
0.8095	Intermediate Similarity	NPC18953
0.8095	Intermediate Similarity	NPC473299
0.809	Intermediate Similarity	NPC151214
0.809	Intermediate Similarity	NPC191915
0.8072	Intermediate Similarity	NPC477284
0.8068	Intermediate Similarity	NPC475878
0.8043	Intermediate Similarity	NPC471426
0.8043	Intermediate Similarity	NPC471427
0.8043	Intermediate Similarity	NPC51579
0.8043	Intermediate Similarity	NPC471428
0.8	Intermediate Similarity	NPC94582
0.8	Intermediate Similarity	NPC57964
0.7978	Intermediate Similarity	NPC163902
0.7978	Intermediate Similarity	NPC35164
0.7931	Intermediate Similarity	NPC221993
0.7931	Intermediate Similarity	NPC470872
0.7927	Intermediate Similarity	NPC220379
0.7912	Intermediate Similarity	NPC252056
0.7912	Intermediate Similarity	NPC296936
0.7912	Intermediate Similarity	NPC145553
0.7907	Intermediate Similarity	NPC471369
0.7882	Intermediate Similarity	NPC471367
0.7849	Intermediate Similarity	NPC470030
0.7841	Intermediate Similarity	NPC82955
0.7826	Intermediate Similarity	NPC470591
0.7816	Intermediate Similarity	NPC140446
0.7816	Intermediate Similarity	NPC62202
0.7816	Intermediate Similarity	NPC43912
0.7816	Intermediate Similarity	NPC110365
0.7816	Intermediate Similarity	NPC45833
0.7816	Intermediate Similarity	NPC213658
0.7805	Intermediate Similarity	NPC477577
0.7802	Intermediate Similarity	NPC21897
0.7791	Intermediate Similarity	NPC290612
0.7778	Intermediate Similarity	NPC470623
0.7778	Intermediate Similarity	NPC323231
0.7778	Intermediate Similarity	NPC171741
0.7778	Intermediate Similarity	NPC18724
0.7778	Intermediate Similarity	NPC224003
0.7766	Intermediate Similarity	NPC476512
0.7766	Intermediate Similarity	NPC472081
0.7766	Intermediate Similarity	NPC475574
0.7766	Intermediate Similarity	NPC108227
0.7765	Intermediate Similarity	NPC473742
0.7753	Intermediate Similarity	NPC473542
0.7753	Intermediate Similarity	NPC50443
0.7753	Intermediate Similarity	NPC18536
0.775	Intermediate Similarity	NPC74639
0.7742	Intermediate Similarity	NPC292775
0.7738	Intermediate Similarity	NPC271572
0.7738	Intermediate Similarity	NPC474870
0.7727	Intermediate Similarity	NPC281004
0.7717	Intermediate Similarity	NPC475765
0.7717	Intermediate Similarity	NPC156377
0.7717	Intermediate Similarity	NPC8954
0.7717	Intermediate Similarity	NPC94905
0.7717	Intermediate Similarity	NPC475785
0.7711	Intermediate Similarity	NPC476176
0.7711	Intermediate Similarity	NPC73013
0.7701	Intermediate Similarity	NPC215968
0.7701	Intermediate Similarity	NPC477283
0.7701	Intermediate Similarity	NPC471368
0.7701	Intermediate Similarity	NPC155531
0.7692	Intermediate Similarity	NPC253611
0.7692	Intermediate Similarity	NPC148593
0.7692	Intermediate Similarity	NPC77717
0.7692	Intermediate Similarity	NPC267238
0.7692	Intermediate Similarity	NPC471373
0.7684	Intermediate Similarity	NPC134967
0.7684	Intermediate Similarity	NPC114700
0.7684	Intermediate Similarity	NPC470029
0.7684	Intermediate Similarity	NPC310138
0.7683	Intermediate Similarity	NPC212453
0.7667	Intermediate Similarity	NPC229801
0.7667	Intermediate Similarity	NPC149966
0.7667	Intermediate Similarity	NPC5632
0.7667	Intermediate Similarity	NPC307167
0.7667	Intermediate Similarity	NPC210759
0.766	Intermediate Similarity	NPC146188
0.7647	Intermediate Similarity	NPC296734
0.7647	Intermediate Similarity	NPC286719
0.7647	Intermediate Similarity	NPC477286
0.764	Intermediate Similarity	NPC102725
0.764	Intermediate Similarity	NPC20822
0.764	Intermediate Similarity	NPC473472
0.764	Intermediate Similarity	NPC131466
0.7634	Intermediate Similarity	NPC472273
0.7634	Intermediate Similarity	NPC210157
0.7634	Intermediate Similarity	NPC97867
0.7625	Intermediate Similarity	NPC123122
0.7619	Intermediate Similarity	NPC472943
0.7619	Intermediate Similarity	NPC472951
0.7614	Intermediate Similarity	NPC252714
0.7609	Intermediate Similarity	NPC471429
0.7609	Intermediate Similarity	NPC205129
0.7609	Intermediate Similarity	NPC106701
0.7609	Intermediate Similarity	NPC189575
0.7609	Intermediate Similarity	NPC471424
0.7609	Intermediate Similarity	NPC471425
0.7604	Intermediate Similarity	NPC97260
0.7604	Intermediate Similarity	NPC476837
0.7604	Intermediate Similarity	NPC139181
0.759	Intermediate Similarity	NPC177343
0.7582	Intermediate Similarity	NPC122083
0.7582	Intermediate Similarity	NPC311246
0.7582	Intermediate Similarity	NPC182740
0.7582	Intermediate Similarity	NPC211845
0.7582	Intermediate Similarity	NPC12297
0.7582	Intermediate Similarity	NPC256104
0.7582	Intermediate Similarity	NPC88962
0.7582	Intermediate Similarity	NPC144790
0.7582	Intermediate Similarity	NPC475307
0.7582	Intermediate Similarity	NPC167644
0.7582	Intermediate Similarity	NPC149400
0.7579	Intermediate Similarity	NPC476838
0.7579	Intermediate Similarity	NPC476839
0.7568	Intermediate Similarity	NPC204173
0.7558	Intermediate Similarity	NPC111582
0.7558	Intermediate Similarity	NPC477285
0.7556	Intermediate Similarity	NPC65550
0.7556	Intermediate Similarity	NPC223143
0.7556	Intermediate Similarity	NPC279329
0.7551	Intermediate Similarity	NPC126753
0.7531	Intermediate Similarity	NPC55508
0.7529	Intermediate Similarity	NPC470154
0.7529	Intermediate Similarity	NPC190940
0.7528	Intermediate Similarity	NPC144069
0.7528	Intermediate Similarity	NPC263079
0.7526	Intermediate Similarity	NPC469827
0.75	Intermediate Similarity	NPC475436
0.75	Intermediate Similarity	NPC113500
0.75	Intermediate Similarity	NPC473774
0.75	Intermediate Similarity	NPC473851
0.75	Intermediate Similarity	NPC24960
0.75	Intermediate Similarity	NPC252253
0.75	Intermediate Similarity	NPC45959
0.75	Intermediate Similarity	NPC253268
0.75	Intermediate Similarity	NPC179859
0.75	Intermediate Similarity	NPC80640
0.75	Intermediate Similarity	NPC174024
0.75	Intermediate Similarity	NPC291547
0.75	Intermediate Similarity	NPC312678
0.75	Intermediate Similarity	NPC305418
0.75	Intermediate Similarity	NPC3538
0.75	Intermediate Similarity	NPC131693
0.75	Intermediate Similarity	NPC477224
0.75	Intermediate Similarity	NPC175
0.7475	Intermediate Similarity	NPC207693
0.7474	Intermediate Similarity	NPC317019
0.7474	Intermediate Similarity	NPC80417
0.7473	Intermediate Similarity	NPC473830
0.7473	Intermediate Similarity	NPC476668
0.7473	Intermediate Similarity	NPC36372
0.7473	Intermediate Similarity	NPC293609
0.7473	Intermediate Similarity	NPC59006
0.7473	Intermediate Similarity	NPC204881
0.7473	Intermediate Similarity	NPC473637
0.7447	Intermediate Similarity	NPC471770
0.7447	Intermediate Similarity	NPC278939
0.7447	Intermediate Similarity	NPC266417
0.7447	Intermediate Similarity	NPC472145
0.7447	Intermediate Similarity	NPC473555
0.7444	Intermediate Similarity	NPC471459
0.7444	Intermediate Similarity	NPC67653
0.7442	Intermediate Similarity	NPC470611
0.7442	Intermediate Similarity	NPC477447
0.7442	Intermediate Similarity	NPC60018
0.7442	Intermediate Similarity	NPC154043
0.7442	Intermediate Similarity	NPC477446
0.7442	Intermediate Similarity	NPC202688
0.7442	Intermediate Similarity	NPC470155
0.7439	Intermediate Similarity	NPC478105
0.7419	Intermediate Similarity	NPC473065
0.7419	Intermediate Similarity	NPC473067
0.7419	Intermediate Similarity	NPC473064
0.7412	Intermediate Similarity	NPC7479
0.7412	Intermediate Similarity	NPC248944

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 NPC475456 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	441
0.1-0.2	4362
0.2-0.3	3052
0.3-0.4	717
0.4-0.5	333
0.5-0.6	169
0.6-0.7	66
0.7-0.8	10
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
0.7412	Intermediate Similarity	NPD6928	Phase 2
0.7391	Intermediate Similarity	NPD8171	Discontinued
0.7	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6118	Approved
0.6977	Remote Similarity	NPD6114	Approved
0.6977	Remote Similarity	NPD6115	Approved
0.6977	Remote Similarity	NPD6697	Approved
0.6951	Remote Similarity	NPD2254	Approved
0.6951	Remote Similarity	NPD2686	Approved
0.6951	Remote Similarity	NPD2687	Approved
0.686	Remote Similarity	NPD6116	Phase 1
0.6778	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3669	Approved
0.6744	Remote Similarity	NPD6117	Approved
0.6742	Remote Similarity	NPD1780	Approved
0.6742	Remote Similarity	NPD1779	Approved
0.6737	Remote Similarity	NPD8035	Phase 2
0.6737	Remote Similarity	NPD8034	Phase 2
0.6731	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7991	Discontinued
0.6667	Remote Similarity	NPD5777	Approved
0.6636	Remote Similarity	NPD8133	Approved
0.6606	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD1810	Approved
0.6512	Remote Similarity	NPD1811	Approved
0.6512	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8294	Approved
0.6429	Remote Similarity	NPD7900	Approved
0.6429	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8377	Approved
0.6429	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD7328	Approved
0.6396	Remote Similarity	NPD7327	Approved
0.6372	Remote Similarity	NPD8379	Approved
0.6372	Remote Similarity	NPD8296	Approved
0.6372	Remote Similarity	NPD8380	Approved
0.6372	Remote Similarity	NPD8335	Approved
0.6372	Remote Similarity	NPD8378	Approved
0.6372	Remote Similarity	NPD8033	Approved
0.6364	Remote Similarity	NPD6940	Discontinued
0.6353	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7516	Approved
0.6277	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD7748	Approved
0.6261	Remote Similarity	NPD8328	Phase 3
0.625	Remote Similarity	NPD3703	Phase 2
0.6238	Remote Similarity	NPD7902	Approved
0.6186	Remote Similarity	NPD7736	Approved
0.6176	Remote Similarity	NPD7638	Approved
0.6117	Remote Similarity	NPD7639	Approved
0.6117	Remote Similarity	NPD7640	Approved
0.6092	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD6412	Phase 2
0.6047	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD8308	Discontinued
0.6019	Remote Similarity	NPD6686	Approved
0.6017	Remote Similarity	NPD7507	Approved
0.6	Remote Similarity	NPD7632	Discontinued
0.5978	Remote Similarity	NPD7645	Phase 2
0.5966	Remote Similarity	NPD8293	Discontinued
0.5948	Remote Similarity	NPD7503	Approved
0.5909	Remote Similarity	NPD6081	Approved
0.59	Remote Similarity	NPD7515	Phase 2
0.5889	Remote Similarity	NPD3702	Approved
0.5882	Remote Similarity	NPD4224	Phase 2
0.5868	Remote Similarity	NPD7319	Approved
0.5833	Remote Similarity	NPD6008	Approved
0.581	Remote Similarity	NPD8418	Phase 2
0.5795	Remote Similarity	NPD4787	Phase 1
0.5795	Remote Similarity	NPD4244	Approved
0.5795	Remote Similarity	NPD4245	Approved
0.578	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD6370	Approved
0.5761	Remote Similarity	NPD8143	Approved
0.5761	Remote Similarity	NPD8144	Approved
0.5758	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD229	Approved
0.5747	Remote Similarity	NPD5360	Phase 3
0.5745	Remote Similarity	NPD7525	Registered
0.5727	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD6399	Phase 3
0.5682	Remote Similarity	NPD3698	Phase 2
0.5676	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD7492	Approved
0.5664	Remote Similarity	NPD6882	Approved
0.5648	Remote Similarity	NPD7912	Approved
0.5648	Remote Similarity	NPD7986	Approved
0.5648	Remote Similarity	NPD7987	Approved
0.5648	Remote Similarity	NPD7911	Approved
0.5647	Remote Similarity	NPD371	Approved
0.5625	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.562	Remote Similarity	NPD6616	Approved
0.5618	Remote Similarity	NPD4789	Approved
0.5607	Remote Similarity	NPD1700	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