NPASS Compound

Structure

CID281540 OpenBabel06191716092D 21 24 0 0 1 0 0 0 0 0999 V2000 2.5073 -0.4461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6722 -2.8938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8364 -2.4116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6700 -0.9648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6703 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1778 -1.4457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6714 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3425 -0.9634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8356 0.4827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3431 -2.8933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5078 -2.4111 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1781 -2.4106 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8361 -1.4466 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9644 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6717 -0.9639 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8358 0.4822 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5075 -1.4461 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0443 -2.9102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 1.4822 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 4 1 0 0 0 0 3 12 1 0 0 0 0 5 6 1 0 0 0 0 5 15 1 0 0 0 0 6 17 1 0 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 12 18 1 1 0 0 0 13 20 1 6 0 0 0 14 4 1 1 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 19 1 6 0 0 0 16 18 1 6 0 0 0 17 19 1 6 0 0 0 17 21 1 0 0 0 0 18 1 1 6 0 0 0 19 2 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.24
Volume:	320.535
LogP:	3.993
LogD:	3.998
LogS:	-1.988
# Rotatable Bonds:	0
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.714
Synthetic Accessibility Score:	4.007
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.678
MDCK Permeability:	1.619706927158404e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.963
30% Bioavailability (F30%):	0.914

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.286
Plasma Protein Binding (PPB):	82.6589584350586%
Volume Distribution (VD):	0.889
Pgp-substrate:	7.791680335998535%

ADMET: Metabolism

CYP1A2-inhibitor:	0.12
CYP1A2-substrate:	0.352
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.8
CYP2C9-inhibitor:	0.055
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.278
CYP3A4-inhibitor:	0.243
CYP3A4-substrate:	0.227

ADMET: Excretion

Clearance (CL):	18.458
Half-life (T1/2):	0.512

ADMET: Toxicity

hERG Blockers:	0.327
Human Hepatotoxicity (H-HT):	0.462
Drug-inuced Liver Injury (DILI):	0.197
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.167
Maximum Recommended Daily Dose:	0.63
Skin Sensitization:	0.965
Carcinogencity:	0.45
Eye Corrosion:	0.989
Eye Irritation:	0.641
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC281540

Natural Product ID:	NPC281540
*Common Name:**	(3S,5R,8R,9S,10S,13S,14S,17S)-10,13-Dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-Tetradecahydro-1H-Cyclopenta[A]Phenanthrene-3,17-Diol
IUPAC Name:	(3S,5R,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
Synonyms:	5Beta-Androstane-3Beta,17Betadiol
Standard InCHIKey:	CBMYJHIOYJEBSB-VXZRPZIYSA-N
Standard InCHI:	InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13+,14+,15+,16+,17+,18+,19+/m1/s1
SMILES:	C[C@]12CC[C@@H](C[C@H]1CC[C@H]1[C@@H]3CC[C@@H]([C@@]3(C)CC[C@H]21)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1908037
PubChem CID:	9922115
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003568] Androstane steroids [CHEMONTID:0001467] Androgens and derivatives

*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

☑ 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
Potency	3

Activity Type	# Activity
Individual Protein	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	5804.8	nM	PMID[497218]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[497218]
NPT2	Others	Unspecified		Potency	n.a.	6309.6	nM	PMID[497218]
NPT697	Individual Protein	UDP-glucuronosyltransferase 2B7	Homo sapiens	Activity	=	5.0	total picomoles	PMID[497219]

☑ 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 NPC281540 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	341
0.1-0.2	4652
0.2-0.3	18016
0.3-0.4	8098
0.4-0.5	4956
0.5-0.6	4182
0.6-0.7	1830
0.7-0.8	468
0.8-0.85	96
0.85-0.9	37
0.9-0.95	15
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC167995
1.0	High Similarity	NPC118937
1.0	High Similarity	NPC159654
0.9672	High Similarity	NPC44122
0.95	High Similarity	NPC114891
0.9333	High Similarity	NPC218585
0.9333	High Similarity	NPC71460
0.9333	High Similarity	NPC148174
0.9219	High Similarity	NPC477820
0.9077	High Similarity	NPC63588
0.9077	High Similarity	NPC251201
0.9077	High Similarity	NPC232925
0.9048	High Similarity	NPC142712
0.9032	High Similarity	NPC69149
0.8906	High Similarity	NPC475884
0.8906	High Similarity	NPC48079
0.8906	High Similarity	NPC473230
0.8906	High Similarity	NPC63190
0.8889	High Similarity	NPC473276
0.8889	High Similarity	NPC41577
0.8889	High Similarity	NPC474380
0.8889	High Similarity	NPC190827
0.8889	High Similarity	NPC243469
0.8889	High Similarity	NPC475943
0.8833	High Similarity	NPC476735
0.8806	High Similarity	NPC470610
0.8806	High Similarity	NPC153719
0.8769	High Similarity	NPC472741
0.8676	High Similarity	NPC304499
0.8676	High Similarity	NPC477508
0.8676	High Similarity	NPC48795
0.8636	High Similarity	NPC129829
0.8636	High Similarity	NPC107919
0.8636	High Similarity	NPC241085
0.8636	High Similarity	NPC66407
0.8636	High Similarity	NPC254037
0.8636	High Similarity	NPC470830
0.8636	High Similarity	NPC299948
0.8571	High Similarity	NPC236099
0.8571	High Similarity	NPC249078
0.8571	High Similarity	NPC209686
0.8551	High Similarity	NPC317242
0.8507	High Similarity	NPC231945
0.8507	High Similarity	NPC192192
0.8507	High Similarity	NPC282454
0.8485	Intermediate Similarity	NPC474756
0.8429	Intermediate Similarity	NPC163597
0.8429	Intermediate Similarity	NPC470145
0.8382	Intermediate Similarity	NPC151018
0.8382	Intermediate Similarity	NPC320549
0.8382	Intermediate Similarity	NPC470071
0.8382	Intermediate Similarity	NPC127094
0.8382	Intermediate Similarity	NPC252182
0.8382	Intermediate Similarity	NPC109457
0.8382	Intermediate Similarity	NPC156277
0.8382	Intermediate Similarity	NPC473279
0.8382	Intermediate Similarity	NPC187471
0.8382	Intermediate Similarity	NPC195530
0.8382	Intermediate Similarity	NPC100586
0.8382	Intermediate Similarity	NPC1340
0.8382	Intermediate Similarity	NPC58057
0.8382	Intermediate Similarity	NPC478103
0.8382	Intermediate Similarity	NPC157422
0.8361	Intermediate Similarity	NPC135438
0.8358	Intermediate Similarity	NPC213178
0.8358	Intermediate Similarity	NPC327728
0.8358	Intermediate Similarity	NPC6120
0.8358	Intermediate Similarity	NPC131892
0.8358	Intermediate Similarity	NPC321732
0.8358	Intermediate Similarity	NPC324607
0.831	Intermediate Similarity	NPC476233
0.831	Intermediate Similarity	NPC192046
0.831	Intermediate Similarity	NPC105208
0.831	Intermediate Similarity	NPC302578
0.831	Intermediate Similarity	NPC477227
0.831	Intermediate Similarity	NPC128951
0.831	Intermediate Similarity	NPC185915
0.8308	Intermediate Similarity	NPC80463
0.8308	Intermediate Similarity	NPC260116
0.8281	Intermediate Similarity	NPC292419
0.8281	Intermediate Similarity	NPC290791
0.8261	Intermediate Similarity	NPC473238
0.8261	Intermediate Similarity	NPC310766
0.8261	Intermediate Similarity	NPC232112
0.8261	Intermediate Similarity	NPC472341
0.8194	Intermediate Similarity	NPC42853
0.8194	Intermediate Similarity	NPC477817
0.8194	Intermediate Similarity	NPC67657
0.8194	Intermediate Similarity	NPC18857
0.8194	Intermediate Similarity	NPC477819
0.8169	Intermediate Similarity	NPC38141
0.8143	Intermediate Similarity	NPC10476
0.8143	Intermediate Similarity	NPC228994
0.8143	Intermediate Similarity	NPC478130
0.8143	Intermediate Similarity	NPC192501
0.8143	Intermediate Similarity	NPC254340
0.8143	Intermediate Similarity	NPC280026
0.8143	Intermediate Similarity	NPC167702
0.8116	Intermediate Similarity	NPC111234
0.8116	Intermediate Similarity	NPC131506
0.8116	Intermediate Similarity	NPC89310
0.8116	Intermediate Similarity	NPC157777
0.8088	Intermediate Similarity	NPC99264
0.8082	Intermediate Similarity	NPC49627
0.8082	Intermediate Similarity	NPC287452
0.8082	Intermediate Similarity	NPC49599
0.8065	Intermediate Similarity	NPC236588
0.806	Intermediate Similarity	NPC204233
0.8056	Intermediate Similarity	NPC138502
0.8056	Intermediate Similarity	NPC307336
0.8056	Intermediate Similarity	NPC260301
0.803	Intermediate Similarity	NPC477603
0.803	Intermediate Similarity	NPC472946
0.8028	Intermediate Similarity	NPC91387
0.8028	Intermediate Similarity	NPC3403
0.8028	Intermediate Similarity	NPC273366
0.8028	Intermediate Similarity	NPC97534
0.8028	Intermediate Similarity	NPC231680
0.8028	Intermediate Similarity	NPC103822
0.8028	Intermediate Similarity	NPC240235
0.8028	Intermediate Similarity	NPC195155
0.8028	Intermediate Similarity	NPC70982
0.8028	Intermediate Similarity	NPC178383
0.8028	Intermediate Similarity	NPC243027
0.8028	Intermediate Similarity	NPC212733
0.8028	Intermediate Similarity	NPC212879
0.8028	Intermediate Similarity	NPC104387
0.8028	Intermediate Similarity	NPC196136
0.8028	Intermediate Similarity	NPC185536
0.8028	Intermediate Similarity	NPC174964
0.8028	Intermediate Similarity	NPC270306
0.8028	Intermediate Similarity	NPC231256
0.8028	Intermediate Similarity	NPC230704
0.8028	Intermediate Similarity	NPC158208
0.8	Intermediate Similarity	NPC472506
0.8	Intermediate Similarity	NPC195489
0.7973	Intermediate Similarity	NPC78545
0.7973	Intermediate Similarity	NPC248944
0.7973	Intermediate Similarity	NPC7479
0.7973	Intermediate Similarity	NPC257296
0.7973	Intermediate Similarity	NPC71535
0.7973	Intermediate Similarity	NPC470609
0.7971	Intermediate Similarity	NPC45296
0.7945	Intermediate Similarity	NPC471045
0.7945	Intermediate Similarity	NPC472501
0.7945	Intermediate Similarity	NPC472499
0.7945	Intermediate Similarity	NPC472500
0.7941	Intermediate Similarity	NPC469987
0.7941	Intermediate Similarity	NPC475893
0.7937	Intermediate Similarity	NPC162685
0.7917	Intermediate Similarity	NPC14112
0.7917	Intermediate Similarity	NPC473916
0.7917	Intermediate Similarity	NPC472487
0.7917	Intermediate Similarity	NPC86305
0.7917	Intermediate Similarity	NPC477601
0.7917	Intermediate Similarity	NPC477602
0.7917	Intermediate Similarity	NPC278091
0.7917	Intermediate Similarity	NPC472486
0.7917	Intermediate Similarity	NPC4209
0.7917	Intermediate Similarity	NPC91573
0.7917	Intermediate Similarity	NPC475742
0.7917	Intermediate Similarity	NPC5767
0.7917	Intermediate Similarity	NPC93662
0.7917	Intermediate Similarity	NPC78067
0.7903	Intermediate Similarity	NPC3025
0.7887	Intermediate Similarity	NPC5046
0.7887	Intermediate Similarity	NPC62657
0.7887	Intermediate Similarity	NPC472854
0.7887	Intermediate Similarity	NPC145552
0.7887	Intermediate Similarity	NPC476736
0.7887	Intermediate Similarity	NPC196358
0.7887	Intermediate Similarity	NPC472503
0.7887	Intermediate Similarity	NPC254509
0.7887	Intermediate Similarity	NPC475458
0.7887	Intermediate Similarity	NPC25511
0.7887	Intermediate Similarity	NPC192638
0.7887	Intermediate Similarity	NPC133922
0.7887	Intermediate Similarity	NPC49168
0.7887	Intermediate Similarity	NPC308440
0.7867	Intermediate Similarity	NPC469745
0.7857	Intermediate Similarity	NPC127283
0.7857	Intermediate Similarity	NPC164045
0.7857	Intermediate Similarity	NPC8004
0.7846	Intermediate Similarity	NPC185547
0.7846	Intermediate Similarity	NPC95804
0.7838	Intermediate Similarity	NPC476176
0.7838	Intermediate Similarity	NPC1319
0.7838	Intermediate Similarity	NPC24504
0.7838	Intermediate Similarity	NPC476316
0.7826	Intermediate Similarity	NPC210323
0.7826	Intermediate Similarity	NPC470833
0.7812	Intermediate Similarity	NPC95958
0.7808	Intermediate Similarity	NPC202540
0.7808	Intermediate Similarity	NPC317913
0.7808	Intermediate Similarity	NPC143133
0.7808	Intermediate Similarity	NPC23884
0.7808	Intermediate Similarity	NPC171658
0.7808	Intermediate Similarity	NPC331618
0.7808	Intermediate Similarity	NPC212241
0.7808	Intermediate Similarity	NPC257191

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 NPC281540 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	359
0.1-0.2	4374
0.2-0.3	3194
0.3-0.4	709
0.4-0.5	189
0.5-0.6	215
0.6-0.7	75
0.7-0.8	23
0.8-0.85	5
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9077	High Similarity	NPD4787	Phase 1
0.8636	High Similarity	NPD4267	Clinical (unspecified phase)
0.8507	High Similarity	NPD4244	Approved
0.8507	High Similarity	NPD4245	Approved
0.8382	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8358	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8358	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8358	Intermediate Similarity	NPD3698	Phase 2
0.8143	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD6928	Phase 2
0.7917	Intermediate Similarity	NPD6117	Approved
0.7808	Intermediate Similarity	NPD6116	Phase 1
0.7778	Intermediate Similarity	NPD3703	Phase 2
0.7714	Intermediate Similarity	NPD4789	Approved
0.7703	Intermediate Similarity	NPD6115	Approved
0.7703	Intermediate Similarity	NPD6118	Approved
0.7703	Intermediate Similarity	NPD6114	Approved
0.7703	Intermediate Similarity	NPD6697	Approved
0.7681	Intermediate Similarity	NPD5360	Phase 3
0.7681	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7525	Registered
0.7467	Intermediate Similarity	NPD3671	Phase 1
0.7361	Intermediate Similarity	NPD5777	Approved
0.7297	Intermediate Similarity	NPD7339	Approved
0.7297	Intermediate Similarity	NPD6942	Approved
0.7273	Intermediate Similarity	NPD4748	Discontinued
0.7183	Intermediate Similarity	NPD6705	Phase 1
0.7123	Intermediate Similarity	NPD4758	Discontinued
0.7067	Intermediate Similarity	NPD3702	Approved
0.7037	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4788	Approved
0.7	Intermediate Similarity	NPD385	Approved
0.7	Intermediate Similarity	NPD384	Approved
0.6923	Remote Similarity	NPD7645	Phase 2
0.6901	Remote Similarity	NPD4224	Phase 2
0.6892	Remote Similarity	NPD4243	Approved
0.6892	Remote Similarity	NPD6081	Approved
0.686	Remote Similarity	NPD8171	Discontinued
0.6795	Remote Similarity	NPD5364	Discontinued
0.6711	Remote Similarity	NPD4785	Approved
0.6711	Remote Similarity	NPD6924	Approved
0.6711	Remote Similarity	NPD6926	Approved
0.6711	Remote Similarity	NPD4784	Approved
0.6707	Remote Similarity	NPD4786	Approved
0.6707	Remote Similarity	NPD3665	Phase 1
0.6707	Remote Similarity	NPD3133	Approved
0.6707	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3667	Approved
0.6628	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6700	Approved
0.6552	Remote Similarity	NPD6702	Approved
0.6552	Remote Similarity	NPD6703	Approved
0.6548	Remote Similarity	NPD3618	Phase 1
0.6538	Remote Similarity	NPD6933	Approved
0.6522	Remote Similarity	NPD3198	Approved
0.6517	Remote Similarity	NPD7991	Discontinued
0.6512	Remote Similarity	NPD5328	Approved
0.6477	Remote Similarity	NPD4202	Approved
0.6447	Remote Similarity	NPD7152	Approved
0.6447	Remote Similarity	NPD7150	Approved
0.6447	Remote Similarity	NPD7151	Approved
0.641	Remote Similarity	NPD5275	Approved
0.641	Remote Similarity	NPD4190	Phase 3
0.64	Remote Similarity	NPD6922	Approved
0.64	Remote Similarity	NPD6923	Approved
0.6364	Remote Similarity	NPD8034	Phase 2
0.6364	Remote Similarity	NPD8035	Phase 2
0.6364	Remote Similarity	NPD6079	Approved
0.6316	Remote Similarity	NPD7143	Approved
0.6316	Remote Similarity	NPD7144	Approved
0.6304	Remote Similarity	NPD7638	Approved
0.6296	Remote Similarity	NPD6929	Approved
0.6296	Remote Similarity	NPD4195	Approved
0.629	Remote Similarity	NPD388	Approved
0.629	Remote Similarity	NPD386	Approved
0.6237	Remote Similarity	NPD7640	Approved
0.6237	Remote Similarity	NPD7639	Approved
0.622	Remote Similarity	NPD7509	Discontinued
0.622	Remote Similarity	NPD6931	Approved
0.622	Remote Similarity	NPD6930	Phase 2
0.6196	Remote Similarity	NPD7920	Phase 3
0.6196	Remote Similarity	NPD7919	Phase 3
0.6196	Remote Similarity	NPD4755	Approved
0.6164	Remote Similarity	NPD371	Approved
0.6163	Remote Similarity	NPD8308	Discontinued
0.6146	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD4753	Phase 2
0.6129	Remote Similarity	NPD8088	Phase 1
0.6105	Remote Similarity	NPD7632	Discontinued
0.6071	Remote Similarity	NPD4223	Phase 3
0.6071	Remote Similarity	NPD4221	Approved
0.6064	Remote Similarity	NPD5286	Approved
0.6064	Remote Similarity	NPD4700	Approved
0.6064	Remote Similarity	NPD8418	Phase 2
0.6064	Remote Similarity	NPD5285	Approved
0.6064	Remote Similarity	NPD4696	Approved
0.6049	Remote Similarity	NPD5776	Phase 2
0.6049	Remote Similarity	NPD6932	Approved
0.6049	Remote Similarity	NPD6925	Approved
0.6047	Remote Similarity	NPD5329	Approved
0.6023	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.602	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD6695	Phase 3
0.6	Remote Similarity	NPD7515	Phase 2
0.6	Remote Similarity	NPD4159	Approved
0.5977	Remote Similarity	NPD5330	Approved
0.5977	Remote Similarity	NPD7334	Approved
0.5977	Remote Similarity	NPD7521	Approved
0.5977	Remote Similarity	NPD7146	Approved
0.5977	Remote Similarity	NPD6409	Approved
0.5977	Remote Similarity	NPD6684	Approved
0.5976	Remote Similarity	NPD3617	Approved
0.5976	Remote Similarity	NPD7145	Approved
0.5952	Remote Similarity	NPD4692	Approved
0.5952	Remote Similarity	NPD4139	Approved
0.5938	Remote Similarity	NPD5224	Approved
0.5938	Remote Similarity	NPD5226	Approved
0.5938	Remote Similarity	NPD5225	Approved
0.5938	Remote Similarity	NPD5211	Phase 2
0.5938	Remote Similarity	NPD4633	Approved
0.5934	Remote Similarity	NPD6399	Phase 3
0.593	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.593	Remote Similarity	NPD3668	Phase 3
0.593	Remote Similarity	NPD4197	Approved
0.5918	Remote Similarity	NPD6402	Approved
0.5918	Remote Similarity	NPD7128	Approved
0.5918	Remote Similarity	NPD6675	Approved
0.5918	Remote Similarity	NPD5739	Approved
0.5914	Remote Similarity	NPD5221	Approved
0.5914	Remote Similarity	NPD4697	Phase 3
0.5914	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD5222	Approved
0.5904	Remote Similarity	NPD6683	Phase 2
0.5876	Remote Similarity	NPD5175	Approved
0.5876	Remote Similarity	NPD4754	Approved
0.5876	Remote Similarity	NPD5174	Approved
0.5862	Remote Similarity	NPD6893	Approved
0.5857	Remote Similarity	NPD586	Phase 1
0.5851	Remote Similarity	NPD5173	Approved
0.5851	Remote Similarity	NPD6084	Phase 2
0.5851	Remote Similarity	NPD6083	Phase 2
0.5843	Remote Similarity	NPD6903	Approved
0.5833	Remote Similarity	NPD7514	Phase 3
0.5816	Remote Similarity	NPD5141	Approved
0.5806	Remote Similarity	NPD5210	Approved
0.5806	Remote Similarity	NPD4629	Approved
0.5802	Remote Similarity	NPD8264	Approved
0.58	Remote Similarity	NPD6899	Approved
0.58	Remote Similarity	NPD7320	Approved
0.58	Remote Similarity	NPD6881	Approved
0.5795	Remote Similarity	NPD4689	Approved
0.5795	Remote Similarity	NPD5205	Approved
0.5795	Remote Similarity	NPD4690	Approved
0.5795	Remote Similarity	NPD4138	Approved
0.5795	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD4693	Phase 3
0.5795	Remote Similarity	NPD4688	Approved
0.5795	Remote Similarity	NPD5279	Phase 3
0.5789	Remote Similarity	NPD5290	Discontinued
0.5783	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD6051	Approved
0.5765	Remote Similarity	NPD6902	Approved
0.5758	Remote Similarity	NPD4768	Approved
0.5758	Remote Similarity	NPD6920	Discontinued
0.5758	Remote Similarity	NPD4767	Approved
0.5743	Remote Similarity	NPD6373	Approved
0.5743	Remote Similarity	NPD6372	Approved
0.573	Remote Similarity	NPD7524	Approved
0.573	Remote Similarity	NPD7750	Discontinued
0.57	Remote Similarity	NPD5697	Approved
0.57	Remote Similarity	NPD5701	Approved
0.5699	Remote Similarity	NPD7748	Approved
0.5686	Remote Similarity	NPD7102	Approved
0.5686	Remote Similarity	NPD6883	Approved
0.5686	Remote Similarity	NPD7290	Approved
0.5679	Remote Similarity	NPD1810	Approved
0.5679	Remote Similarity	NPD1811	Approved
0.5667	Remote Similarity	NPD4723	Approved
0.5667	Remote Similarity	NPD4722	Approved
0.5647	Remote Similarity	NPD7332	Phase 2
0.5644	Remote Similarity	NPD5128	Approved
0.5644	Remote Similarity	NPD6011	Approved
0.5644	Remote Similarity	NPD6415	Discontinued
0.5644	Remote Similarity	NPD4729	Approved
0.5644	Remote Similarity	NPD4730	Approved
0.5631	Remote Similarity	NPD6650	Approved
0.5631	Remote Similarity	NPD6649	Approved
0.5631	Remote Similarity	NPD6847	Approved
0.5631	Remote Similarity	NPD8130	Phase 1
0.5631	Remote Similarity	NPD6617	Approved
0.5631	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD6869	Approved
0.5618	Remote Similarity	NPD4694	Approved
0.5618	Remote Similarity	NPD5690	Phase 2
0.5618	Remote Similarity	NPD5280	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