NPASS Compound

Structure

NPC271163 OpenBabel07101719512D 30 34 0 0 1 0 0 0 0 0999 V2000 -3.7497 3.2753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7624 3.3056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2901 4.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8179 1.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2517 2.7517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2517 0.0817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8179 3.3056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8179 2.3611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0892 1.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6358 1.8889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8179 2.3611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8259 3.0790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5340 2.1807 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8179 2.3611 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 3.7778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5340 0.6526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6358 0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.8889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8179 3.3056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.8889 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6358 1.8889 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6358 0.9444 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.9444 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8179 0.4722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1939 3.7808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.7222 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8259 -0.2456 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2717 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6358 2.8333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 22 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 20 1 0 0 0 0 9 13 1 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 25 2 0 0 0 0 13 21 1 6 0 0 0 14 19 1 0 0 0 0 14 20 1 1 0 0 0 15 19 1 0 0 0 0 15 26 2 0 0 0 0 16 22 1 0 0 0 0 16 27 2 0 0 0 0 17 28 2 0 0 0 0 18 23 1 0 0 0 0 18 29 2 0 0 0 0 20 23 1 6 0 0 0 21 22 1 6 0 0 0 22 24 1 6 0 0 0 23 24 1 1 0 0 0 23 30 1 0 0 0 0 24 17 1 6 0 0 0 24 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.2
Volume:	420.437
LogP:	2.231
LogD:	1.78
LogS:	-4.636
# Rotatable Bonds:	1
TPSA:	97.88
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.612
Synthetic Accessibility Score:	5.268
Fsp3:	0.792
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.411
MDCK Permeability:	2.4453926016576588e-05
Pgp-inhibitor:	0.515
Pgp-substrate:	0.022
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.945

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.96
Plasma Protein Binding (PPB):	62.835445404052734%
Volume Distribution (VD):	0.476
Pgp-substrate:	33.88069152832031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.982
CYP2C19-inhibitor:	0.097
CYP2C19-substrate:	0.925
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.127
CYP3A4-substrate:	0.928

ADMET: Excretion

Clearance (CL):	7.118
Half-life (T1/2):	0.76

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.357
Drug-inuced Liver Injury (DILI):	0.861
AMES Toxicity:	0.992
Rat Oral Acute Toxicity:	0.62
Maximum Recommended Daily Dose:	0.055
Skin Sensitization:	0.936
Carcinogencity:	0.971
Eye Corrosion:	0.04
Eye Irritation:	0.271
Respiratory Toxicity:	0.801

Download Data

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

Natural Product: NPC271163

Natural Product ID:	NPC271163
*Common Name:**	NZNMCSYRDNCBPL-BNAOJXJXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NZNMCSYRDNCBPL-BNAOJXJXSA-N
Standard InCHI:	InChI=1S/C24H30O6/c1-12(25)13-9-16(27)22(6)21(13,5)11-18(29)23-20(4)8-7-15(26)19(2,3)14(20)10-17(28)24(22,23)30-23/h13-14H,7-11H2,1-6H3/t13-,14+,20+,21-,22-,23+,24+/m1/s1
SMILES:	CC(=O)[C@H]1CC(=O)[C@@]2([C@]1(C)CC(=O)[C@]13[C@]2(O1)C(=O)C[C@@H]1[C@]3(C)CCC(=O)C1(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461271
PubChem CID:	636904
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO33360	ganoderma concinna	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11908995]

☑ 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
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	12.0	%	PMID[479297]

☑ 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 NPC271163 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	503
0.1-0.2	5314
0.2-0.3	13926
0.3-0.4	10675
0.4-0.5	6525
0.5-0.6	4375
0.6-0.7	1232
0.7-0.8	145
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8152	Intermediate Similarity	NPC476294
0.7955	Intermediate Similarity	NPC90676
0.7901	Intermediate Similarity	NPC72444
0.7778	Intermediate Similarity	NPC476296
0.759	Intermediate Similarity	NPC471046
0.7586	Intermediate Similarity	NPC472847
0.7556	Intermediate Similarity	NPC477614
0.7556	Intermediate Similarity	NPC226491
0.7529	Intermediate Similarity	NPC275243
0.7528	Intermediate Similarity	NPC120395
0.75	Intermediate Similarity	NPC475689
0.7473	Intermediate Similarity	NPC61688
0.7471	Intermediate Similarity	NPC13494
0.7471	Intermediate Similarity	NPC328007
0.7447	Intermediate Similarity	NPC62407
0.7447	Intermediate Similarity	NPC287354
0.7439	Intermediate Similarity	NPC474123
0.7419	Intermediate Similarity	NPC474379
0.7419	Intermediate Similarity	NPC228700
0.7386	Intermediate Similarity	NPC327451
0.7381	Intermediate Similarity	NPC472487
0.7381	Intermediate Similarity	NPC472486
0.7368	Intermediate Similarity	NPC477264
0.7349	Intermediate Similarity	NPC133922
0.734	Intermediate Similarity	NPC247877
0.734	Intermediate Similarity	NPC309127
0.7317	Intermediate Similarity	NPC197701
0.7317	Intermediate Similarity	NPC472309
0.7303	Intermediate Similarity	NPC319909
0.7303	Intermediate Similarity	NPC474996
0.7303	Intermediate Similarity	NPC50438
0.7294	Intermediate Similarity	NPC471151
0.7283	Intermediate Similarity	NPC11611
0.7263	Intermediate Similarity	NPC470031
0.7262	Intermediate Similarity	NPC125767
0.7262	Intermediate Similarity	NPC21220
0.7216	Intermediate Similarity	NPC109059
0.7216	Intermediate Similarity	NPC288
0.7174	Intermediate Similarity	NPC236459
0.7158	Intermediate Similarity	NPC477495
0.7143	Intermediate Similarity	NPC80700
0.7143	Intermediate Similarity	NPC254340
0.7143	Intermediate Similarity	NPC248216
0.7143	Intermediate Similarity	NPC476727
0.7143	Intermediate Similarity	NPC477441
0.7143	Intermediate Similarity	NPC476726
0.7126	Intermediate Similarity	NPC320144
0.7125	Intermediate Similarity	NPC84562
0.7111	Intermediate Similarity	NPC105895
0.7111	Intermediate Similarity	NPC181871
0.7111	Intermediate Similarity	NPC9060
0.7111	Intermediate Similarity	NPC471044
0.7111	Intermediate Similarity	NPC473336
0.7108	Intermediate Similarity	NPC473267
0.7108	Intermediate Similarity	NPC311102
0.7108	Intermediate Similarity	NPC89310
0.7093	Intermediate Similarity	NPC221420
0.7093	Intermediate Similarity	NPC475031
0.7093	Intermediate Similarity	NPC23884
0.7093	Intermediate Similarity	NPC477918
0.7083	Intermediate Similarity	NPC17336
0.7079	Intermediate Similarity	NPC289486
0.7079	Intermediate Similarity	NPC317066
0.7079	Intermediate Similarity	NPC61107
0.7079	Intermediate Similarity	NPC30583
0.7073	Intermediate Similarity	NPC196197
0.7065	Intermediate Similarity	NPC263802
0.7059	Intermediate Similarity	NPC472311
0.7059	Intermediate Similarity	NPC273366
0.7059	Intermediate Similarity	NPC159789
0.7053	Intermediate Similarity	NPC472148
0.7053	Intermediate Similarity	NPC472147
0.7053	Intermediate Similarity	NPC476189
0.7045	Intermediate Similarity	NPC1882
0.7033	Intermediate Similarity	NPC473350
0.7033	Intermediate Similarity	NPC474572
0.7024	Intermediate Similarity	NPC232112
0.7024	Intermediate Similarity	NPC248567
0.7011	Intermediate Similarity	NPC475725
0.7011	Intermediate Similarity	NPC478128
0.7011	Intermediate Similarity	NPC185465
0.6977	Remote Similarity	NPC475742
0.6977	Remote Similarity	NPC5767
0.697	Remote Similarity	NPC156324
0.697	Remote Similarity	NPC55503
0.6966	Remote Similarity	NPC58631
0.6966	Remote Similarity	NPC50658
0.6957	Remote Similarity	NPC302111
0.6951	Remote Similarity	NPC470956
0.6951	Remote Similarity	NPC473225
0.6947	Remote Similarity	NPC216137
0.6939	Remote Similarity	NPC190080
0.6939	Remote Similarity	NPC111187
0.6939	Remote Similarity	NPC216904
0.6932	Remote Similarity	NPC472310
0.6931	Remote Similarity	NPC266
0.6923	Remote Similarity	NPC321661
0.6923	Remote Similarity	NPC320475
0.6923	Remote Similarity	NPC25037
0.6923	Remote Similarity	NPC34984
0.6915	Remote Similarity	NPC471459
0.6915	Remote Similarity	NPC67653
0.6915	Remote Similarity	NPC200580
0.6915	Remote Similarity	NPC24705
0.6915	Remote Similarity	NPC56962
0.6907	Remote Similarity	NPC266431
0.6905	Remote Similarity	NPC156277
0.6905	Remote Similarity	NPC320549
0.6905	Remote Similarity	NPC126642
0.6905	Remote Similarity	NPC58057
0.6905	Remote Similarity	NPC151018
0.69	Remote Similarity	NPC60947
0.6897	Remote Similarity	NPC474404
0.6889	Remote Similarity	NPC268040
0.6882	Remote Similarity	NPC202937
0.6875	Remote Similarity	NPC128608
0.6869	Remote Similarity	NPC112753
0.6869	Remote Similarity	NPC275439
0.6867	Remote Similarity	NPC131892
0.6867	Remote Similarity	NPC327728
0.6867	Remote Similarity	NPC6120
0.6867	Remote Similarity	NPC213178
0.686	Remote Similarity	NPC174964
0.686	Remote Similarity	NPC97534
0.686	Remote Similarity	NPC195155
0.686	Remote Similarity	NPC477934
0.6854	Remote Similarity	NPC477851
0.6854	Remote Similarity	NPC125366
0.6854	Remote Similarity	NPC261616
0.6848	Remote Similarity	NPC62572
0.6848	Remote Similarity	NPC224345
0.6842	Remote Similarity	NPC477442
0.6842	Remote Similarity	NPC477433
0.6842	Remote Similarity	NPC477444
0.6837	Remote Similarity	NPC476728
0.6837	Remote Similarity	NPC140242
0.6837	Remote Similarity	NPC165616
0.6829	Remote Similarity	NPC328304
0.6829	Remote Similarity	NPC329466
0.6827	Remote Similarity	NPC316930
0.6824	Remote Similarity	NPC474755
0.6824	Remote Similarity	NPC109510
0.6813	Remote Similarity	NPC15821
0.6813	Remote Similarity	NPC268578
0.6813	Remote Similarity	NPC292458
0.6813	Remote Similarity	NPC217559
0.6809	Remote Similarity	NPC131104
0.6809	Remote Similarity	NPC3032
0.6809	Remote Similarity	NPC473319
0.6786	Remote Similarity	NPC476731
0.6782	Remote Similarity	NPC477933
0.6782	Remote Similarity	NPC4209
0.6782	Remote Similarity	NPC477932
0.6778	Remote Similarity	NPC472229
0.6778	Remote Similarity	NPC472230
0.6778	Remote Similarity	NPC469745
0.6778	Remote Similarity	NPC12933
0.6774	Remote Similarity	NPC92139
0.6774	Remote Similarity	NPC471042
0.6771	Remote Similarity	NPC250753
0.6771	Remote Similarity	NPC327515
0.6771	Remote Similarity	NPC52756
0.6771	Remote Similarity	NPC470230
0.6768	Remote Similarity	NPC23680
0.6768	Remote Similarity	NPC470632
0.6765	Remote Similarity	NPC70967
0.6765	Remote Similarity	NPC33973
0.6765	Remote Similarity	NPC216114
0.6747	Remote Similarity	NPC475977
0.6744	Remote Similarity	NPC55508
0.6744	Remote Similarity	NPC272359
0.6742	Remote Similarity	NPC73013
0.6742	Remote Similarity	NPC80891
0.6742	Remote Similarity	NPC52951
0.6742	Remote Similarity	NPC201276
0.6739	Remote Similarity	NPC219535
0.6739	Remote Similarity	NPC477434
0.6739	Remote Similarity	NPC237938
0.6737	Remote Similarity	NPC477443
0.6737	Remote Similarity	NPC477440
0.6737	Remote Similarity	NPC472234
0.6737	Remote Similarity	NPC472233
0.6737	Remote Similarity	NPC473039
0.6735	Remote Similarity	NPC305808
0.6733	Remote Similarity	NPC124211
0.6731	Remote Similarity	NPC176949
0.6731	Remote Similarity	NPC201908
0.6707	Remote Similarity	NPC268736
0.6707	Remote Similarity	NPC477931
0.6706	Remote Similarity	NPC469940
0.6705	Remote Similarity	NPC207010
0.6705	Remote Similarity	NPC264602
0.6705	Remote Similarity	NPC317913
0.6705	Remote Similarity	NPC169389
0.6705	Remote Similarity	NPC143250
0.6703	Remote Similarity	NPC476935
0.6703	Remote Similarity	NPC477936
0.6703	Remote Similarity	NPC477935
0.6703	Remote Similarity	NPC258153
0.6703	Remote Similarity	NPC476458

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 NPC271163 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	513
0.1-0.2	4521
0.2-0.3	2956
0.3-0.4	681
0.4-0.5	215
0.5-0.6	188
0.6-0.7	68
0.7-0.8	8
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
0.7375	Intermediate Similarity	NPD5360	Phase 3
0.7375	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4758	Discontinued
0.7108	Intermediate Similarity	NPD6081	Approved
0.7059	Intermediate Similarity	NPD3703	Phase 2
0.6988	Remote Similarity	NPD4789	Approved
0.6905	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5364	Discontinued
0.6782	Remote Similarity	NPD6117	Approved
0.6707	Remote Similarity	NPD4224	Phase 2
0.6706	Remote Similarity	NPD5777	Approved
0.6705	Remote Similarity	NPD6116	Phase 1
0.6667	Remote Similarity	NPD3702	Approved
0.6629	Remote Similarity	NPD6114	Approved
0.6629	Remote Similarity	NPD6115	Approved
0.6629	Remote Similarity	NPD6118	Approved
0.6629	Remote Similarity	NPD6697	Approved
0.6585	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD1700	Approved
0.6552	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4697	Phase 3
0.6471	Remote Similarity	NPD3698	Phase 2
0.6449	Remote Similarity	NPD6372	Approved
0.6449	Remote Similarity	NPD6373	Approved
0.6429	Remote Similarity	NPD8035	Phase 2
0.6429	Remote Similarity	NPD8034	Phase 2
0.6421	Remote Similarity	NPD6098	Approved
0.6421	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4244	Approved
0.6395	Remote Similarity	NPD4245	Approved
0.6392	Remote Similarity	NPD6904	Approved
0.6392	Remote Similarity	NPD6673	Approved
0.6392	Remote Similarity	NPD6080	Approved
0.6373	Remote Similarity	NPD5696	Approved
0.633	Remote Similarity	NPD6649	Approved
0.633	Remote Similarity	NPD6650	Approved
0.6321	Remote Similarity	NPD7128	Approved
0.6321	Remote Similarity	NPD5739	Approved
0.6321	Remote Similarity	NPD6402	Approved
0.6321	Remote Similarity	NPD6008	Approved
0.6321	Remote Similarity	NPD6675	Approved
0.6289	Remote Similarity	NPD6672	Approved
0.6289	Remote Similarity	NPD5737	Approved
0.6275	Remote Similarity	NPD4755	Approved
0.6264	Remote Similarity	NPD3671	Phase 1
0.6263	Remote Similarity	NPD5693	Phase 1
0.6262	Remote Similarity	NPD5701	Approved
0.6262	Remote Similarity	NPD5697	Approved
0.6238	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6881	Approved
0.6204	Remote Similarity	NPD7320	Approved
0.6204	Remote Similarity	NPD6899	Approved
0.6204	Remote Similarity	NPD6011	Approved
0.6176	Remote Similarity	NPD5221	Approved
0.6176	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5222	Approved
0.6162	Remote Similarity	NPD5692	Phase 3
0.6154	Remote Similarity	NPD4696	Approved
0.6154	Remote Similarity	NPD5285	Approved
0.6154	Remote Similarity	NPD5286	Approved
0.6154	Remote Similarity	NPD4700	Approved
0.6147	Remote Similarity	NPD6012	Approved
0.6147	Remote Similarity	NPD6013	Approved
0.6147	Remote Similarity	NPD6014	Approved
0.6139	Remote Similarity	NPD6001	Approved
0.6117	Remote Similarity	NPD5173	Approved
0.61	Remote Similarity	NPD6050	Approved
0.61	Remote Similarity	NPD5694	Approved
0.6095	Remote Similarity	NPD5223	Approved
0.6092	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD7102	Approved
0.6091	Remote Similarity	NPD7290	Approved
0.6091	Remote Similarity	NPD6883	Approved
0.6087	Remote Similarity	NPD3617	Approved
0.6078	Remote Similarity	NPD5210	Approved
0.6078	Remote Similarity	NPD4629	Approved
0.6061	Remote Similarity	NPD5328	Approved
0.6042	Remote Similarity	NPD4197	Approved
0.604	Remote Similarity	NPD6399	Phase 3
0.6038	Remote Similarity	NPD5211	Phase 2
0.6038	Remote Similarity	NPD5224	Approved
0.6038	Remote Similarity	NPD5226	Approved
0.6038	Remote Similarity	NPD4633	Approved
0.6038	Remote Similarity	NPD5225	Approved
0.6036	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD6847	Approved
0.6036	Remote Similarity	NPD8130	Phase 1
0.6036	Remote Similarity	NPD6869	Approved
0.6036	Remote Similarity	NPD6617	Approved
0.602	Remote Similarity	NPD3573	Approved
0.5982	Remote Similarity	NPD6882	Approved
0.5982	Remote Similarity	NPD8297	Approved
0.5981	Remote Similarity	NPD4754	Approved
0.5981	Remote Similarity	NPD5174	Approved
0.5981	Remote Similarity	NPD5175	Approved
0.5979	Remote Similarity	NPD5329	Approved
0.5979	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD6614	Approved
0.5962	Remote Similarity	NPD6084	Phase 2
0.5962	Remote Similarity	NPD6083	Phase 2
0.5962	Remote Similarity	NPD5959	Approved
0.5946	Remote Similarity	NPD4634	Approved
0.5941	Remote Similarity	NPD6079	Approved
0.5938	Remote Similarity	NPD4788	Approved
0.5926	Remote Similarity	NPD5141	Approved
0.5922	Remote Similarity	NPD5654	Approved
0.5922	Remote Similarity	NPD5695	Phase 3
0.5918	Remote Similarity	NPD3618	Phase 1
0.5909	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.59	Remote Similarity	NPD4753	Phase 2
0.5897	Remote Similarity	NPD6319	Approved
0.5897	Remote Similarity	NPD6059	Approved
0.5897	Remote Similarity	NPD6054	Approved
0.5872	Remote Similarity	NPD6920	Discontinued
0.5872	Remote Similarity	NPD4767	Approved
0.5872	Remote Similarity	NPD4768	Approved
0.5847	Remote Similarity	NPD6016	Approved
0.5847	Remote Similarity	NPD6015	Approved
0.5833	Remote Similarity	NPD4221	Approved
0.5833	Remote Similarity	NPD4223	Phase 3
0.5826	Remote Similarity	NPD6274	Approved
0.5825	Remote Similarity	NPD7900	Approved
0.5825	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.58	Remote Similarity	NPD5208	Approved
0.5798	Remote Similarity	NPD6370	Approved
0.5798	Remote Similarity	NPD5988	Approved
0.578	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD6317	Approved
0.5776	Remote Similarity	NPD7115	Discovery
0.5766	Remote Similarity	NPD5128	Approved
0.5766	Remote Similarity	NPD4730	Approved
0.5766	Remote Similarity	NPD4729	Approved
0.5758	Remote Similarity	NPD4694	Approved
0.5758	Remote Similarity	NPD5280	Approved
0.5758	Remote Similarity	NPD5690	Phase 2
0.5741	Remote Similarity	NPD5091	Approved
0.5729	Remote Similarity	NPD4139	Approved
0.5729	Remote Similarity	NPD4692	Approved
0.5728	Remote Similarity	NPD4202	Approved
0.5726	Remote Similarity	NPD6313	Approved
0.5726	Remote Similarity	NPD6314	Approved
0.5726	Remote Similarity	NPD6335	Approved
0.5714	Remote Similarity	NPD3668	Phase 3
0.5714	Remote Similarity	NPD4786	Approved
0.5702	Remote Similarity	NPD7492	Approved
0.5691	Remote Similarity	NPD7736	Approved
0.569	Remote Similarity	NPD6868	Approved
0.5686	Remote Similarity	NPD5207	Approved
0.5678	Remote Similarity	NPD7101	Approved
0.5678	Remote Similarity	NPD7100	Approved
0.567	Remote Similarity	NPD3667	Approved
0.5667	Remote Similarity	NPD4787	Phase 1
0.5664	Remote Similarity	NPD5251	Approved
0.5664	Remote Similarity	NPD5169	Approved
0.5664	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD5248	Approved
0.5664	Remote Similarity	NPD5249	Phase 3
0.5664	Remote Similarity	NPD5247	Approved
0.5664	Remote Similarity	NPD5135	Approved
0.5664	Remote Similarity	NPD5250	Approved
0.566	Remote Similarity	NPD7902	Approved
0.5656	Remote Similarity	NPD6616	Approved
0.5652	Remote Similarity	NPD4632	Approved
0.5644	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD6009	Approved
0.5625	Remote Similarity	NPD5168	Approved
0.562	Remote Similarity	NPD7604	Phase 2
0.5618	Remote Similarity	NPD229	Approved
0.5614	Remote Similarity	NPD5216	Approved
0.5614	Remote Similarity	NPD5215	Approved
0.5614	Remote Similarity	NPD5127	Approved
0.5614	Remote Similarity	NPD5217	Approved
0.561	Remote Similarity	NPD8293	Discontinued
0.561	Remote Similarity	NPD7078	Approved
0.56	Remote Similarity	NPD7521	Approved
0.56	Remote Similarity	NPD4688	Approved
0.56	Remote Similarity	NPD5330	Approved
0.56	Remote Similarity	NPD4690	Approved
0.56	Remote Similarity	NPD4689	Approved
0.56	Remote Similarity	NPD4693	Phase 3
0.56	Remote Similarity	NPD4138	Approved
0.56	Remote Similarity	NPD5205	Approved
0.56	Remote Similarity	NPD6684	Approved
0.56	Remote Similarity	NPD7146	Approved
0.56	Remote Similarity	NPD6409	Approved
0.56	Remote Similarity	NPD7334	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