NPASS Compound

Structure

NPC473637 OpenBabel07101718272D 44 48 0 0 1 0 0 0 0 0999 V2000 11.2220 -6.4671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4994 -6.2861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0904 -3.1215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0963 -2.4265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6131 -3.1092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7949 -4.7038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7085 -4.2970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1942 -1.8085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0474 -2.7356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1453 -2.1175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9984 -3.0446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6590 -3.4558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7690 -5.0520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8645 -5.5009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5536 -2.0823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4130 -5.8793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9859 -4.1160 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.4511 -2.4776 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.5121 -4.3828 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.3042 -3.4047 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.0724 -4.5227 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.6100 -3.7648 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.8179 -4.7430 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 11.7446 -1.4945 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.5175 -4.8848 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.8699 -5.6054 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.4632 -4.6919 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.8311 -1.9013 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.7265 -2.8958 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 11.5356 -3.4836 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.3532 -3.0957 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.2063 -4.0227 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.5000 -2.1686 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0748 -5.4121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8491 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0221 -1.3135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8130 -3.3025 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3699 -7.4714 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 3.3699 -6.4714 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3699 -5.4714 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.4491 -3.0768 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.4310 -4.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3699 -6.4714 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3699 -6.4714 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 31 1 0 0 0 0 5 32 1 0 0 0 0 6 7 1 0 0 0 0 6 17 1 0 0 0 0 7 25 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 10 31 1 0 0 0 0 11 32 1 0 0 0 0 12 18 1 0 0 0 0 12 22 1 0 0 0 0 13 19 1 0 0 0 0 13 23 1 0 0 0 0 14 21 1 0 0 0 0 14 26 1 0 0 0 0 15 24 1 0 0 0 0 15 41 1 0 0 0 0 16 25 1 0 0 0 0 17 21 1 0 0 0 0 18 33 1 0 0 0 0 19 20 1 0 0 0 0 19 27 1 0 0 0 0 20 31 1 0 0 0 0 21 32 1 0 0 0 0 22 23 1 0 0 0 0 22 31 1 0 0 0 0 23 34 1 0 0 0 0 24 28 1 0 0 0 0 24 35 1 0 0 0 0 25 42 1 0 0 0 0 26 27 1 0 0 0 0 26 43 1 0 0 0 0 27 32 1 0 0 0 0 28 29 1 0 0 0 0 28 36 1 0 0 0 0 29 30 1 0 0 0 0 29 37 1 0 0 0 0 30 41 1 0 0 0 0 30 42 1 0 0 0 0 38 44 1 0 0 0 0 39 44 2 0 0 0 0 40 44 2 0 0 0 0 43 44 1 0 0 0 0 M CHG 1 38 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	647.35
Volume:	633.129
LogP:	3.55
LogD:	3.861
LogS:	-3.36
# Rotatable Bonds:	9
TPSA:	186.04
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.183
Synthetic Accessibility Score:	5.727
Fsp3:	1.0
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:	-4.984
MDCK Permeability:	2.054192555078771e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.901
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.232

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	94.65413665771484%
Volume Distribution (VD):	0.795
Pgp-substrate:	4.712870121002197%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.586
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.747
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.096

ADMET: Excretion

Clearance (CL):	2.055
Half-life (T1/2):	0.147

ADMET: Toxicity

hERG Blockers:	0.775
Human Hepatotoxicity (H-HT):	0.328
Drug-inuced Liver Injury (DILI):	0.105
AMES Toxicity:	0.098
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.373
Skin Sensitization:	0.955
Carcinogencity:	0.443
Eye Corrosion:	0.034
Eye Irritation:	0.061
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC473637

Natural Product ID:	NPC473637
*Common Name:**	Amurensoside A
IUPAC Name:	sodium;[(3S,5S,6S,8R,9S,10R,13R,14S,15S,17R)-3,6-dihydroxy-10,13-dimethyl-17-[(2R,5S)-6-methyl-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-15-yl] sulfate
Synonyms:
Standard InCHIKey:	VLNAJFRHGTVSIU-KVWIOHKVSA-M
Standard InCHI:	InChI=1S/C32H56O11S.Na/c1-16(2)25(42-30-29(37)28(36)24(35)15-41-30)7-6-17(3)21-14-26(43-44(38,39)40)27-19-13-23(34)22-12-18(33)8-10-31(22,4)20(19)9-11-32(21,27)5;/h16-30,33-37H,6-15H2,1-5H3,(H,38,39,40);/q;+1/p-1/t17-,18+,19-,20+,21-,22-,23+,24-,25+,26+,27-,28+,29-,30+,31-,32-;/m1./s1
SMILES:	CC(C)C(CCC(C)C1CC(C2C1(CCC3C2CC(C4C3(CCC(C4)O)C)O)C)OS(=O)(=O)[O-])OC5C(C(C(CO5)O)O)O.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447797
PubChem CID:	44560016
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*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
NPO9446	Asterias rathbuni	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473430]
NPO9446	Asterias rathbuni	Species	Asteriidae	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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		IC100	=	1.9	10'-4M	PMID[464220]

☑ 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 NPC473637 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	531
0.1-0.2	4965
0.2-0.3	13650
0.3-0.4	10832
0.4-0.5	5403
0.5-0.6	3717
0.6-0.7	2355
0.7-0.8	948
0.8-0.85	136
0.85-0.9	130
0.9-0.95	22
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476668
0.9884	High Similarity	NPC476669
0.977	High Similarity	NPC475325
0.977	High Similarity	NPC473503
0.9659	High Similarity	NPC469710
0.9647	High Similarity	NPC281004
0.9551	High Similarity	NPC473287
0.9535	High Similarity	NPC473472
0.9535	High Similarity	NPC102725
0.9425	High Similarity	NPC65550
0.9425	High Similarity	NPC279329
0.9425	High Similarity	NPC223143
0.9425	High Similarity	NPC473542
0.9341	High Similarity	NPC473616
0.9341	High Similarity	NPC473638
0.9318	High Similarity	NPC5632
0.9318	High Similarity	NPC149966
0.9318	High Similarity	NPC204881
0.9318	High Similarity	NPC473830
0.9318	High Similarity	NPC293609
0.9318	High Similarity	NPC36372
0.9302	High Similarity	NPC43912
0.9302	High Similarity	NPC140446
0.9213	High Similarity	NPC144790
0.9213	High Similarity	NPC149400
0.9213	High Similarity	NPC172838
0.9213	High Similarity	NPC137004
0.9213	High Similarity	NPC88962
0.9213	High Similarity	NPC473726
0.9213	High Similarity	NPC167644
0.9213	High Similarity	NPC311246
0.9213	High Similarity	NPC277774
0.914	High Similarity	NPC477225
0.9111	High Similarity	NPC291547
0.9111	High Similarity	NPC309866
0.9111	High Similarity	NPC253268
0.9111	High Similarity	NPC475436
0.9111	High Similarity	NPC3538
0.9111	High Similarity	NPC24960
0.9111	High Similarity	NPC45959
0.9111	High Similarity	NPC312678
0.9111	High Similarity	NPC179859
0.9111	High Similarity	NPC113500
0.9111	High Similarity	NPC174024
0.9111	High Similarity	NPC131693
0.9111	High Similarity	NPC473851
0.9111	High Similarity	NPC175
0.9111	High Similarity	NPC252253
0.9111	High Similarity	NPC477224
0.9111	High Similarity	NPC473774
0.9091	High Similarity	NPC131466
0.9091	High Similarity	NPC20822
0.9091	High Similarity	NPC82955
0.907	High Similarity	NPC290612
0.9011	High Similarity	NPC473065
0.9011	High Similarity	NPC473067
0.9011	High Similarity	NPC92196
0.9011	High Similarity	NPC473064
0.9	High Similarity	NPC234352
0.9	High Similarity	NPC48339
0.9	High Similarity	NPC325828
0.9	High Similarity	NPC250393
0.9	High Similarity	NPC297348
0.9	High Similarity	NPC177834
0.9	High Similarity	NPC141769
0.9	High Similarity	NPC477451
0.9	High Similarity	NPC477547
0.9	High Similarity	NPC249204
0.8913	High Similarity	NPC296936
0.8913	High Similarity	NPC142264
0.8913	High Similarity	NPC139271
0.8913	High Similarity	NPC121453
0.8913	High Similarity	NPC304011
0.8913	High Similarity	NPC476510
0.8901	High Similarity	NPC217205
0.8901	High Similarity	NPC264101
0.8901	High Similarity	NPC471464
0.8901	High Similarity	NPC294686
0.8901	High Similarity	NPC291203
0.8901	High Similarity	NPC222731
0.8889	High Similarity	NPC307167
0.8889	High Similarity	NPC210759
0.8889	High Similarity	NPC229801
0.8817	High Similarity	NPC307534
0.8817	High Similarity	NPC476112
0.8817	High Similarity	NPC477222
0.8817	High Similarity	NPC470591
0.8817	High Similarity	NPC477223
0.8817	High Similarity	NPC475207
0.8817	High Similarity	NPC470028
0.8817	High Similarity	NPC233649
0.8804	High Similarity	NPC473727
0.8804	High Similarity	NPC19400
0.8804	High Similarity	NPC6295
0.8804	High Similarity	NPC474399
0.8804	High Similarity	NPC206003
0.8804	High Similarity	NPC211354
0.8804	High Similarity	NPC473610
0.8804	High Similarity	NPC475351
0.8804	High Similarity	NPC107188
0.8804	High Similarity	NPC107962
0.875	High Similarity	NPC471240
0.8737	High Similarity	NPC478106
0.8723	High Similarity	NPC473518
0.871	High Similarity	NPC84111
0.871	High Similarity	NPC97700
0.871	High Similarity	NPC470863
0.871	High Similarity	NPC103616
0.871	High Similarity	NPC98018
0.871	High Similarity	NPC475643
0.871	High Similarity	NPC232037
0.871	High Similarity	NPC470866
0.871	High Similarity	NPC470865
0.871	High Similarity	NPC128572
0.871	High Similarity	NPC473601
0.871	High Similarity	NPC475625
0.871	High Similarity	NPC132080
0.871	High Similarity	NPC184617
0.871	High Similarity	NPC160426
0.871	High Similarity	NPC287483
0.871	High Similarity	NPC195297
0.871	High Similarity	NPC284104
0.871	High Similarity	NPC470864
0.871	High Similarity	NPC30856
0.871	High Similarity	NPC116756
0.8696	High Similarity	NPC151214
0.8696	High Similarity	NPC191915
0.8696	High Similarity	NPC30687
0.8696	High Similarity	NPC305418
0.8681	High Similarity	NPC59006
0.8652	High Similarity	NPC472396
0.8636	High Similarity	NPC232044
0.8636	High Similarity	NPC273290
0.8632	High Similarity	NPC41843
0.8617	High Similarity	NPC210157
0.8617	High Similarity	NPC51520
0.8617	High Similarity	NPC115165
0.8617	High Similarity	NPC470861
0.8617	High Similarity	NPC303069
0.8617	High Similarity	NPC232611
0.8617	High Similarity	NPC470862
0.8617	High Similarity	NPC83137
0.8617	High Similarity	NPC274200
0.8602	High Similarity	NPC477494
0.8602	High Similarity	NPC57964
0.8602	High Similarity	NPC94582
0.8586	High Similarity	NPC475634
0.8542	High Similarity	NPC476512
0.8542	High Similarity	NPC475574
0.8542	High Similarity	NPC31346
0.8542	High Similarity	NPC472081
0.8542	High Similarity	NPC477172
0.8542	High Similarity	NPC108227
0.8542	High Similarity	NPC476839
0.8542	High Similarity	NPC476838
0.8526	High Similarity	NPC291548
0.8523	High Similarity	NPC227260
0.8523	High Similarity	NPC474156
0.8511	High Similarity	NPC472989
0.8511	High Similarity	NPC203434
0.8511	High Similarity	NPC237071
0.8511	High Similarity	NPC238796
0.8511	High Similarity	NPC252056
0.8506	High Similarity	NPC470611
0.8506	High Similarity	NPC296734
0.85	High Similarity	NPC474573
0.8462	Intermediate Similarity	NPC228059
0.8454	Intermediate Similarity	NPC134967
0.8454	Intermediate Similarity	NPC310138
0.8454	Intermediate Similarity	NPC114700
0.8454	Intermediate Similarity	NPC470029
0.8444	Intermediate Similarity	NPC161928
0.8444	Intermediate Similarity	NPC210658
0.8438	Intermediate Similarity	NPC20028
0.8438	Intermediate Similarity	NPC470030
0.8421	Intermediate Similarity	NPC76486
0.8367	Intermediate Similarity	NPC476837
0.8367	Intermediate Similarity	NPC139181
0.8367	Intermediate Similarity	NPC97260
0.8352	Intermediate Similarity	NPC128475
0.8316	Intermediate Similarity	NPC156377
0.8283	Intermediate Similarity	NPC312774
0.8283	Intermediate Similarity	NPC475365
0.8283	Intermediate Similarity	NPC475521
0.8276	Intermediate Similarity	NPC7479
0.8276	Intermediate Similarity	NPC248944
0.8276	Intermediate Similarity	NPC257296
0.8265	Intermediate Similarity	NPC310031
0.8265	Intermediate Similarity	NPC80191
0.8256	Intermediate Similarity	NPC177343
0.8252	Intermediate Similarity	NPC475354
0.8252	Intermediate Similarity	NPC475312
0.8247	Intermediate Similarity	NPC7341
0.8247	Intermediate Similarity	NPC91497
0.8247	Intermediate Similarity	NPC473200
0.8229	Intermediate Similarity	NPC472273
0.8211	Intermediate Similarity	NPC215570
0.8202	Intermediate Similarity	NPC241959
0.8191	Intermediate Similarity	NPC323231
0.8191	Intermediate Similarity	NPC224003

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 NPC473637 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	495
0.1-0.2	4530
0.2-0.3	2917
0.3-0.4	630
0.4-0.5	301
0.5-0.6	214
0.6-0.7	46
0.7-0.8	15
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD8171	Discontinued
0.8276	Intermediate Similarity	NPD6928	Phase 2
0.81	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7991	Discontinued
0.7257	Intermediate Similarity	NPD8294	Approved
0.7257	Intermediate Similarity	NPD8377	Approved
0.7232	Intermediate Similarity	NPD7327	Approved
0.7232	Intermediate Similarity	NPD7328	Approved
0.7193	Intermediate Similarity	NPD8033	Approved
0.7193	Intermediate Similarity	NPD8378	Approved
0.7193	Intermediate Similarity	NPD8380	Approved
0.7193	Intermediate Similarity	NPD8296	Approved
0.7193	Intermediate Similarity	NPD8379	Approved
0.7193	Intermediate Similarity	NPD8335	Approved
0.7182	Intermediate Similarity	NPD8133	Approved
0.7168	Intermediate Similarity	NPD7516	Approved
0.7	Intermediate Similarity	NPD1811	Approved
0.7	Intermediate Similarity	NPD1810	Approved
0.6944	Remote Similarity	NPD6412	Phase 2
0.6818	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7507	Approved
0.6754	Remote Similarity	NPD6940	Discontinued
0.6752	Remote Similarity	NPD7503	Approved
0.6727	Remote Similarity	NPD8174	Phase 2
0.6702	Remote Similarity	NPD6697	Approved
0.6702	Remote Similarity	NPD6115	Approved
0.6702	Remote Similarity	NPD6118	Approved
0.6702	Remote Similarity	NPD6114	Approved
0.6667	Remote Similarity	NPD2254	Approved
0.6667	Remote Similarity	NPD4787	Phase 1
0.6667	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2687	Approved
0.6667	Remote Similarity	NPD2686	Approved
0.6639	Remote Similarity	NPD7319	Approved
0.6596	Remote Similarity	NPD6116	Phase 1
0.6552	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD3669	Approved
0.6531	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6117	Approved
0.6423	Remote Similarity	NPD7736	Approved
0.6364	Remote Similarity	NPD371	Approved
0.6281	Remote Similarity	NPD6370	Approved
0.6277	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6700	Approved
0.6237	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.623	Remote Similarity	NPD8328	Phase 3
0.6224	Remote Similarity	NPD7525	Registered
0.622	Remote Similarity	NPD8449	Approved
0.6211	Remote Similarity	NPD3703	Phase 2
0.621	Remote Similarity	NPD8293	Discontinued
0.619	Remote Similarity	NPD6702	Approved
0.619	Remote Similarity	NPD6703	Approved
0.619	Remote Similarity	NPD8034	Phase 2
0.619	Remote Similarity	NPD8035	Phase 2
0.6172	Remote Similarity	NPD8450	Suspended
0.614	Remote Similarity	NPD6686	Approved
0.6129	Remote Similarity	NPD4244	Approved
0.6129	Remote Similarity	NPD4245	Approved
0.6116	Remote Similarity	NPD6059	Approved
0.6116	Remote Similarity	NPD6054	Approved
0.6098	Remote Similarity	NPD6067	Discontinued
0.6042	Remote Similarity	NPD3702	Approved
0.6022	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD3698	Phase 2
0.6	Remote Similarity	NPD7638	Approved
0.5946	Remote Similarity	NPD7639	Approved
0.5946	Remote Similarity	NPD7640	Approved
0.5935	Remote Similarity	NPD6016	Approved
0.5935	Remote Similarity	NPD6015	Approved
0.5932	Remote Similarity	NPD8297	Approved
0.5932	Remote Similarity	NPD6882	Approved
0.5922	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.592	Remote Similarity	NPD7492	Approved
0.5895	Remote Similarity	NPD5777	Approved
0.5887	Remote Similarity	NPD5988	Approved
0.5873	Remote Similarity	NPD6616	Approved
0.587	Remote Similarity	NPD7625	Phase 1
0.5868	Remote Similarity	NPD6009	Approved
0.5865	Remote Similarity	NPD8308	Discontinued
0.5859	Remote Similarity	NPD5364	Discontinued
0.5854	Remote Similarity	NPD6319	Approved
0.5843	Remote Similarity	NPD6123	Approved
0.5842	Remote Similarity	NPD1779	Approved
0.5842	Remote Similarity	NPD1780	Approved
0.5841	Remote Similarity	NPD7632	Discontinued
0.5827	Remote Similarity	NPD7078	Approved
0.581	Remote Similarity	NPD7524	Approved
0.58	Remote Similarity	NPD7645	Phase 2
0.5789	Remote Similarity	NPD4789	Approved
0.5766	Remote Similarity	NPD7919	Phase 3
0.5766	Remote Similarity	NPD7920	Phase 3
0.5752	Remote Similarity	NPD1700	Approved
0.575	Remote Similarity	NPD4632	Approved
0.5745	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD5360	Phase 3
0.5739	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8088	Phase 1
0.569	Remote Similarity	NPD7128	Approved
0.569	Remote Similarity	NPD5739	Approved
0.569	Remote Similarity	NPD6402	Approved
0.569	Remote Similarity	NPD6675	Approved
0.5678	Remote Similarity	NPD6373	Approved
0.5678	Remote Similarity	NPD6372	Approved
0.5673	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD8418	Phase 2
0.5659	Remote Similarity	NPD6033	Approved
0.5657	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD2269	Approved
0.5614	Remote Similarity	NPD4159	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