NPASS Compound

Structure

NPC310766 OpenBabel07101718182D 30 33 0 0 1 0 0 0 0 0999 V2000 -1.5180 -4.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1653 -4.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 -1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 -2.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 -3.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 -2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1871 -4.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 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 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 0.5000 0.0000 O 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 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 18 1 0 0 0 0 10 12 1 0 0 0 0 10 20 1 0 0 0 0 11 26 1 0 0 0 0 12 27 1 0 0 0 0 13 18 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 15 21 1 0 0 0 0 15 24 1 0 0 0 0 17 3 1 1 0 0 0 17 25 1 0 0 0 0 18 28 2 0 0 0 0 19 14 1 6 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 26 1 1 0 0 0 21 27 1 1 0 0 0 22 23 1 0 0 0 0 22 26 1 1 0 0 0 23 29 2 0 0 0 0 24 25 1 0 0 0 0 24 30 1 1 0 0 0 25 27 1 1 0 0 0 26 4 1 1 0 0 0 27 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.33
Volume:	462.42
LogP:	5.388
LogD:	5.897
LogS:	-4.852
# Rotatable Bonds:	5
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.614
Synthetic Accessibility Score:	4.594
Fsp3:	0.926
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.798
MDCK Permeability:	1.5804109352757223e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.116
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.981
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.915
Plasma Protein Binding (PPB):	93.60382080078125%
Volume Distribution (VD):	1.048
Pgp-substrate:	1.924730658531189%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.212
CYP2C19-inhibitor:	0.109
CYP2C19-substrate:	0.851
CYP2C9-inhibitor:	0.363
CYP2C9-substrate:	0.19
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.501
CYP3A4-substrate:	0.309

ADMET: Excretion

Clearance (CL):	16.013
Half-life (T1/2):	0.585

ADMET: Toxicity

hERG Blockers:	0.754
Human Hepatotoxicity (H-HT):	0.331
Drug-inuced Liver Injury (DILI):	0.668
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.437
Maximum Recommended Daily Dose:	0.435
Skin Sensitization:	0.671
Carcinogencity:	0.317
Eye Corrosion:	0.05
Eye Irritation:	0.053
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: NPC310766

Natural Product ID:	NPC310766
*Common Name:**	(5S,10R,13S,16S,17R)-17-((R)-1,5-Dimethyl-Hexyl)-16-Hydroxy-10,13-Dimethyl-Tetradecahydro-Cyclopenta[A]Phenanthrene-3,6-Dione
IUPAC Name:	(5S,8R,9S,10R,13S,14S,16S,17R)-16-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,4,5,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,6-dione
Synonyms:
Standard InCHIKey:	VQABOPQARYUTHF-PXICEXDUSA-N
Standard InCHI:	InChI=1S/C27H44O3/c1-16(2)7-6-8-17(3)25-24(30)15-21-19-14-23(29)22-13-18(28)9-11-26(22,4)20(19)10-12-27(21,25)5/h16-17,19-22,24-25,30H,6-15H2,1-5H3/t17-,19-,20+,21+,22-,24+,25+,26-,27+/m1/s1
SMILES:	CC(C)CCC[C@@H](C)[C@H]1[C@H](C[C@H]2[C@@H]3CC(=O)[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3137859
PubChem CID:	11668847
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003566] Cholestane steroids [CHEMONTID:0001469] Cholesterols 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
NPO28315	Jania rubens	Species	Corallinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11086730]
NPO28315	Jania rubens	Species	Corallinaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ID50	=	0.5	ug ml-1	PMID[551992]
NPT91	Cell Line	KB	Homo sapiens	ID50	=	5.0	ug ml-1	PMID[551992]

☑ 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 NPC310766 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	304
0.1-0.2	3439
0.2-0.3	16251
0.3-0.4	8818
0.4-0.5	5577
0.5-0.6	5204
0.6-0.7	2361
0.7-0.8	576
0.8-0.85	106
0.85-0.9	46
0.9-0.95	12
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9552	High Similarity	NPC324607
0.9552	High Similarity	NPC321732
0.9286	High Similarity	NPC472854
0.9275	High Similarity	NPC151018
0.9275	High Similarity	NPC320549
0.9275	High Similarity	NPC58057
0.9275	High Similarity	NPC156277
0.9143	High Similarity	NPC232112
0.9014	High Similarity	NPC254340
0.8986	High Similarity	NPC6120
0.8986	High Similarity	NPC327728
0.8986	High Similarity	NPC131892
0.8986	High Similarity	NPC213178
0.8889	High Similarity	NPC21220
0.8889	High Similarity	NPC27349
0.8889	High Similarity	NPC273366
0.8889	High Similarity	NPC24014
0.8889	High Similarity	NPC195155
0.8889	High Similarity	NPC97534
0.8889	High Similarity	NPC174964
0.8889	High Similarity	NPC125767
0.88	High Similarity	NPC470609
0.8767	High Similarity	NPC475742
0.8767	High Similarity	NPC5767
0.8767	High Similarity	NPC472486
0.8767	High Similarity	NPC472487
0.875	High Similarity	NPC167702
0.875	High Similarity	NPC280026
0.8732	High Similarity	NPC89310
0.8732	High Similarity	NPC473267
0.8714	High Similarity	NPC252032
0.8714	High Similarity	NPC319671
0.8714	High Similarity	NPC469941
0.8714	High Similarity	NPC476734
0.8684	High Similarity	NPC469745
0.8649	High Similarity	NPC180199
0.8649	High Similarity	NPC477919
0.8649	High Similarity	NPC475031
0.8649	High Similarity	NPC23884
0.8649	High Similarity	NPC221420
0.8649	High Similarity	NPC264602
0.863	High Similarity	NPC212733
0.8592	High Similarity	NPC477929
0.8592	High Similarity	NPC476731
0.8571	High Similarity	NPC473225
0.8571	High Similarity	NPC317066
0.8571	High Similarity	NPC328007
0.8533	High Similarity	NPC199965
0.8533	High Similarity	NPC185465
0.8533	High Similarity	NPC476732
0.8514	High Similarity	NPC4209
0.8493	Intermediate Similarity	NPC133922
0.8462	Intermediate Similarity	NPC327451
0.8442	Intermediate Similarity	NPC77311
0.8421	Intermediate Similarity	NPC472310
0.8421	Intermediate Similarity	NPC320144
0.84	Intermediate Similarity	NPC143133
0.84	Intermediate Similarity	NPC298168
0.84	Intermediate Similarity	NPC207010
0.84	Intermediate Similarity	NPC317913
0.84	Intermediate Similarity	NPC474404
0.8378	Intermediate Similarity	NPC472311
0.8378	Intermediate Similarity	NPC159789
0.8333	Intermediate Similarity	NPC108131
0.8333	Intermediate Similarity	NPC477850
0.8312	Intermediate Similarity	NPC472853
0.831	Intermediate Similarity	NPC474954
0.831	Intermediate Similarity	NPC103647
0.831	Intermediate Similarity	NPC180777
0.831	Intermediate Similarity	NPC260319
0.831	Intermediate Similarity	NPC2568
0.8289	Intermediate Similarity	NPC171426
0.8289	Intermediate Similarity	NPC224802
0.8289	Intermediate Similarity	NPC80089
0.8289	Intermediate Similarity	NPC324700
0.8289	Intermediate Similarity	NPC34046
0.8286	Intermediate Similarity	NPC42060
0.8261	Intermediate Similarity	NPC159654
0.8261	Intermediate Similarity	NPC167995
0.8261	Intermediate Similarity	NPC281540
0.8261	Intermediate Similarity	NPC118937
0.8243	Intermediate Similarity	NPC477930
0.8228	Intermediate Similarity	NPC245866
0.8219	Intermediate Similarity	NPC469940
0.8194	Intermediate Similarity	NPC64466
0.8194	Intermediate Similarity	NPC474962
0.8182	Intermediate Similarity	NPC201459
0.8182	Intermediate Similarity	NPC80891
0.8182	Intermediate Similarity	NPC52951
0.8182	Intermediate Similarity	NPC31302
0.8182	Intermediate Similarity	NPC201276
0.8182	Intermediate Similarity	NPC245029
0.8158	Intermediate Similarity	NPC477918
0.8148	Intermediate Similarity	NPC476727
0.8148	Intermediate Similarity	NPC474448
0.8148	Intermediate Similarity	NPC476726
0.8143	Intermediate Similarity	NPC243469
0.8143	Intermediate Similarity	NPC190827
0.8143	Intermediate Similarity	NPC475943
0.8125	Intermediate Similarity	NPC82902
0.8116	Intermediate Similarity	NPC114891
0.8108	Intermediate Similarity	NPC282905
0.8108	Intermediate Similarity	NPC68426
0.8108	Intermediate Similarity	NPC477229
0.8108	Intermediate Similarity	NPC474123
0.8101	Intermediate Similarity	NPC477935
0.8101	Intermediate Similarity	NPC46881
0.8101	Intermediate Similarity	NPC61107
0.8101	Intermediate Similarity	NPC145143
0.8101	Intermediate Similarity	NPC30583
0.8101	Intermediate Similarity	NPC477858
0.8101	Intermediate Similarity	NPC289486
0.806	Intermediate Similarity	NPC476735
0.8052	Intermediate Similarity	NPC329117
0.8028	Intermediate Similarity	NPC44122
0.8028	Intermediate Similarity	NPC268736
0.8028	Intermediate Similarity	NPC477931
0.8026	Intermediate Similarity	NPC477932
0.8026	Intermediate Similarity	NPC108840
0.8026	Intermediate Similarity	NPC477933
0.8025	Intermediate Similarity	NPC474218
0.8	Intermediate Similarity	NPC292458
0.8	Intermediate Similarity	NPC472743
0.8	Intermediate Similarity	NPC217559
0.8	Intermediate Similarity	NPC268578
0.8	Intermediate Similarity	NPC259173
0.8	Intermediate Similarity	NPC472498
0.8	Intermediate Similarity	NPC475726
0.8	Intermediate Similarity	NPC130011
0.8	Intermediate Similarity	NPC168511
0.8	Intermediate Similarity	NPC159325
0.8	Intermediate Similarity	NPC472744
0.7976	Intermediate Similarity	NPC476296
0.7975	Intermediate Similarity	NPC58631
0.7975	Intermediate Similarity	NPC12933
0.7975	Intermediate Similarity	NPC103754
0.7975	Intermediate Similarity	NPC474484
0.7973	Intermediate Similarity	NPC472309
0.7973	Intermediate Similarity	NPC290058
0.7973	Intermediate Similarity	NPC126642
0.7971	Intermediate Similarity	NPC71460
0.7971	Intermediate Similarity	NPC218585
0.7971	Intermediate Similarity	NPC148174
0.7945	Intermediate Similarity	NPC477820
0.7945	Intermediate Similarity	NPC196197
0.7927	Intermediate Similarity	NPC80590
0.7927	Intermediate Similarity	NPC469994
0.7927	Intermediate Similarity	NPC472272
0.7922	Intermediate Similarity	NPC106078
0.7917	Intermediate Similarity	NPC478180
0.7917	Intermediate Similarity	NPC472984
0.7917	Intermediate Similarity	NPC63190
0.7917	Intermediate Similarity	NPC474221
0.7917	Intermediate Similarity	NPC130459
0.7901	Intermediate Similarity	NPC50438
0.7901	Intermediate Similarity	NPC475745
0.7901	Intermediate Similarity	NPC473336
0.7901	Intermediate Similarity	NPC471044
0.7901	Intermediate Similarity	NPC263974
0.7901	Intermediate Similarity	NPC474233
0.7901	Intermediate Similarity	NPC474482
0.7901	Intermediate Similarity	NPC474996
0.7895	Intermediate Similarity	NPC477934
0.7895	Intermediate Similarity	NPC267753
0.7875	Intermediate Similarity	NPC110780
0.7875	Intermediate Similarity	NPC477936
0.7875	Intermediate Similarity	NPC268040
0.7875	Intermediate Similarity	NPC170985
0.7875	Intermediate Similarity	NPC121121
0.7867	Intermediate Similarity	NPC81759
0.7848	Intermediate Similarity	NPC164999
0.7848	Intermediate Similarity	NPC261616
0.7848	Intermediate Similarity	NPC477851
0.7838	Intermediate Similarity	NPC63588
0.7838	Intermediate Similarity	NPC232925
0.7838	Intermediate Similarity	NPC251201
0.7831	Intermediate Similarity	NPC134197
0.7831	Intermediate Similarity	NPC317590
0.7805	Intermediate Similarity	NPC292553
0.7805	Intermediate Similarity	NPC76518
0.7778	Intermediate Similarity	NPC175410
0.7778	Intermediate Similarity	NPC142712
0.7761	Intermediate Similarity	NPC143597
0.7761	Intermediate Similarity	NPC151464
0.7746	Intermediate Similarity	NPC69149
0.7738	Intermediate Similarity	NPC183374
0.7738	Intermediate Similarity	NPC211162
0.7738	Intermediate Similarity	NPC328313
0.7711	Intermediate Similarity	NPC80700
0.7711	Intermediate Similarity	NPC472745
0.7711	Intermediate Similarity	NPC70661
0.7711	Intermediate Similarity	NPC92139
0.7711	Intermediate Similarity	NPC472738
0.7692	Intermediate Similarity	NPC149249
0.7692	Intermediate Similarity	NPC472746
0.7683	Intermediate Similarity	NPC74595
0.7683	Intermediate Similarity	NPC321187
0.7683	Intermediate Similarity	NPC329043
0.7683	Intermediate Similarity	NPC221758
0.7683	Intermediate Similarity	NPC264665

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 NPC310766 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	349
0.1-0.2	3637
0.2-0.3	3681
0.3-0.4	867
0.4-0.5	224
0.5-0.6	196
0.6-0.7	151
0.7-0.8	19
0.8-0.85	9
0.85-0.9	9
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9701	High Similarity	NPD4245	Approved
0.9701	High Similarity	NPD4244	Approved
0.9552	High Similarity	NPD3698	Phase 2
0.9275	High Similarity	NPD4808	Clinical (unspecified phase)
0.9275	High Similarity	NPD4809	Clinical (unspecified phase)
0.913	High Similarity	NPD4789	Approved
0.8986	High Similarity	NPD3699	Clinical (unspecified phase)
0.8986	High Similarity	NPD3700	Clinical (unspecified phase)
0.8955	High Similarity	NPD3171	Clinical (unspecified phase)
0.875	High Similarity	NPD6113	Clinical (unspecified phase)
0.8571	High Similarity	NPD5360	Phase 3
0.8571	High Similarity	NPD5361	Clinical (unspecified phase)
0.8514	High Similarity	NPD6117	Approved
0.8472	Intermediate Similarity	NPD5777	Approved
0.84	Intermediate Similarity	NPD6116	Phase 1
0.8378	Intermediate Similarity	NPD3703	Phase 2
0.8289	Intermediate Similarity	NPD6697	Approved
0.8289	Intermediate Similarity	NPD6118	Approved
0.8289	Intermediate Similarity	NPD6115	Approved
0.8289	Intermediate Similarity	NPD6114	Approved
0.8286	Intermediate Similarity	NPD4224	Phase 2
0.8228	Intermediate Similarity	NPD4788	Approved
0.8219	Intermediate Similarity	NPD6081	Approved
0.8133	Intermediate Similarity	NPD3702	Approved
0.8052	Intermediate Similarity	NPD3671	Phase 1
0.7973	Intermediate Similarity	NPD4758	Discontinued
0.7838	Intermediate Similarity	NPD4787	Phase 1
0.7683	Intermediate Similarity	NPD3665	Phase 1
0.7683	Intermediate Similarity	NPD3133	Approved
0.7683	Intermediate Similarity	NPD3666	Approved
0.7683	Intermediate Similarity	NPD4786	Approved
0.7595	Intermediate Similarity	NPD5364	Discontinued
0.759	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD3667	Approved
0.7429	Intermediate Similarity	NPD3198	Approved
0.7241	Intermediate Similarity	NPD4753	Phase 2
0.7241	Intermediate Similarity	NPD5328	Approved
0.7229	Intermediate Similarity	NPD4221	Approved
0.7229	Intermediate Similarity	NPD4223	Phase 3
0.7191	Intermediate Similarity	NPD4202	Approved
0.7176	Intermediate Similarity	NPD5329	Approved
0.7108	Intermediate Similarity	NPD4139	Approved
0.7108	Intermediate Similarity	NPD4692	Approved
0.7093	Intermediate Similarity	NPD3618	Phase 1
0.7079	Intermediate Similarity	NPD6079	Approved
0.7079	Intermediate Similarity	NPD8035	Phase 2
0.7079	Intermediate Similarity	NPD8034	Phase 2
0.7059	Intermediate Similarity	NPD4197	Approved
0.7	Intermediate Similarity	NPD6399	Phase 3
0.6988	Remote Similarity	NPD6928	Phase 2
0.6951	Remote Similarity	NPD3617	Approved
0.6932	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5205	Approved
0.6897	Remote Similarity	NPD4690	Approved
0.6897	Remote Similarity	NPD5279	Phase 3
0.6897	Remote Similarity	NPD4693	Phase 3
0.6897	Remote Similarity	NPD4688	Approved
0.6897	Remote Similarity	NPD4689	Approved
0.6897	Remote Similarity	NPD7146	Approved
0.6897	Remote Similarity	NPD6409	Approved
0.6897	Remote Similarity	NPD7334	Approved
0.6897	Remote Similarity	NPD5330	Approved
0.6897	Remote Similarity	NPD7521	Approved
0.6897	Remote Similarity	NPD4138	Approved
0.6897	Remote Similarity	NPD6684	Approved
0.6882	Remote Similarity	NPD4755	Approved
0.6882	Remote Similarity	NPD6083	Phase 2
0.6882	Remote Similarity	NPD6084	Phase 2
0.6848	Remote Similarity	NPD4629	Approved
0.6848	Remote Similarity	NPD5210	Approved
0.6804	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4697	Phase 3
0.6742	Remote Similarity	NPD6903	Approved
0.6737	Remote Similarity	NPD5285	Approved
0.6737	Remote Similarity	NPD4700	Approved
0.6737	Remote Similarity	NPD5286	Approved
0.6737	Remote Similarity	NPD4696	Approved
0.6707	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5690	Phase 2
0.6705	Remote Similarity	NPD5280	Approved
0.6705	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD3668	Phase 3
0.6667	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD6705	Phase 1
0.6598	Remote Similarity	NPD5211	Phase 2
0.6598	Remote Similarity	NPD5225	Approved
0.6598	Remote Similarity	NPD5224	Approved
0.6598	Remote Similarity	NPD5226	Approved
0.6598	Remote Similarity	NPD4633	Approved
0.6596	Remote Similarity	NPD5221	Approved
0.6596	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5222	Approved
0.6588	Remote Similarity	NPD7525	Registered
0.6585	Remote Similarity	NPD6942	Approved
0.6585	Remote Similarity	NPD7339	Approved
0.6566	Remote Similarity	NPD5739	Approved
0.6566	Remote Similarity	NPD7128	Approved
0.6566	Remote Similarity	NPD6402	Approved
0.6566	Remote Similarity	NPD6675	Approved
0.6562	Remote Similarity	NPD8418	Phase 2
0.6535	Remote Similarity	NPD6373	Approved
0.6535	Remote Similarity	NPD6372	Approved
0.6531	Remote Similarity	NPD5175	Approved
0.6531	Remote Similarity	NPD4754	Approved
0.6531	Remote Similarity	NPD5174	Approved
0.6526	Remote Similarity	NPD5173	Approved
0.6522	Remote Similarity	NPD7515	Phase 2
0.6517	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6098	Approved
0.6489	Remote Similarity	NPD5695	Phase 3
0.6479	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4195	Approved
0.6465	Remote Similarity	NPD5141	Approved
0.6458	Remote Similarity	NPD5696	Approved
0.6436	Remote Similarity	NPD6899	Approved
0.6436	Remote Similarity	NPD6881	Approved
0.6436	Remote Similarity	NPD7320	Approved
0.642	Remote Similarity	NPD4243	Approved
0.6408	Remote Similarity	NPD6649	Approved
0.6408	Remote Similarity	NPD6650	Approved
0.64	Remote Similarity	NPD6920	Discontinued
0.64	Remote Similarity	NPD4768	Approved
0.64	Remote Similarity	NPD4767	Approved
0.6395	Remote Similarity	NPD4748	Discontinued
0.6374	Remote Similarity	NPD6672	Approved
0.6374	Remote Similarity	NPD5737	Approved
0.6353	Remote Similarity	NPD4238	Approved
0.6353	Remote Similarity	NPD4802	Phase 2
0.6344	Remote Similarity	NPD5281	Approved
0.6344	Remote Similarity	NPD5284	Approved
0.6337	Remote Similarity	NPD5701	Approved
0.6337	Remote Similarity	NPD6412	Phase 2
0.6337	Remote Similarity	NPD5697	Approved
0.6311	Remote Similarity	NPD7102	Approved
0.6311	Remote Similarity	NPD7290	Approved
0.6311	Remote Similarity	NPD6883	Approved
0.6304	Remote Similarity	NPD6904	Approved
0.6304	Remote Similarity	NPD6673	Approved
0.6304	Remote Similarity	NPD6080	Approved
0.6289	Remote Similarity	NPD7638	Approved
0.6277	Remote Similarity	NPD5133	Approved
0.6275	Remote Similarity	NPD5128	Approved
0.6275	Remote Similarity	NPD6415	Discontinued
0.6275	Remote Similarity	NPD6011	Approved
0.6275	Remote Similarity	NPD4729	Approved
0.6275	Remote Similarity	NPD4730	Approved
0.6265	Remote Similarity	NPD6926	Approved
0.6265	Remote Similarity	NPD4785	Approved
0.6265	Remote Similarity	NPD6924	Approved
0.6265	Remote Similarity	NPD4784	Approved
0.625	Remote Similarity	NPD8130	Phase 1
0.625	Remote Similarity	NPD6847	Approved
0.625	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6617	Approved
0.625	Remote Similarity	NPD6869	Approved
0.6237	Remote Similarity	NPD4096	Approved
0.6224	Remote Similarity	NPD7639	Approved
0.6224	Remote Similarity	NPD7640	Approved
0.6214	Remote Similarity	NPD6014	Approved
0.6214	Remote Similarity	NPD6012	Approved
0.6214	Remote Similarity	NPD6013	Approved
0.6211	Remote Similarity	NPD7748	Approved
0.6196	Remote Similarity	NPD5208	Approved
0.619	Remote Similarity	NPD6882	Approved
0.619	Remote Similarity	NPD8297	Approved
0.6186	Remote Similarity	NPD7902	Approved
0.6163	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD4776	Phase 2
0.6163	Remote Similarity	NPD4777	Suspended
0.6154	Remote Similarity	NPD5169	Approved
0.6154	Remote Similarity	NPD5135	Approved
0.6154	Remote Similarity	NPD5248	Approved
0.6154	Remote Similarity	NPD5247	Approved
0.6154	Remote Similarity	NPD5249	Phase 3
0.6154	Remote Similarity	NPD5250	Approved
0.6154	Remote Similarity	NPD5251	Approved
0.6154	Remote Similarity	NPD4634	Approved
0.6154	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD6933	Approved
0.6105	Remote Similarity	NPD8171	Discontinued
0.61	Remote Similarity	NPD7632	Discontinued
0.6098	Remote Similarity	NPD4747	Approved
0.6095	Remote Similarity	NPD5216	Approved
0.6095	Remote Similarity	NPD5215	Approved
0.6095	Remote Similarity	NPD5127	Approved
0.6095	Remote Similarity	NPD5217	Approved
0.6087	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD5368	Approved
0.6023	Remote Similarity	NPD4695	Discontinued
0.6022	Remote Similarity	NPD4518	Approved
0.6	Remote Similarity	NPD5275	Approved
0.6	Remote Similarity	NPD5693	Phase 1
0.6	Remote Similarity	NPD6050	Approved
0.6	Remote Similarity	NPD4190	Phase 3
0.5981	Remote Similarity	NPD4632	Approved
0.5978	Remote Similarity	NPD4623	Approved
0.5978	Remote Similarity	NPD4519	Discontinued

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