NPASS Compound

Structure

CID317066 OpenBabel06191716132D 26 29 0 0 1 0 0 0 0 0999 V2000 3.3604 -0.9332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8399 0.5204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5211 -3.3935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6809 -2.9088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0396 -1.9379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8384 -1.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2000 -1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8387 -0.4852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2005 -3.3930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6801 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9208 1.2689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3610 -2.9083 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0399 -2.9078 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6806 -1.9388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8404 -1.4541 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5202 -0.4843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 0.9690 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5205 -1.4536 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3607 -1.9383 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8402 -0.4847 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 1.1217 2.2168 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9106 -3.4100 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3906 0.0186 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7210 1.6169 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8662 0.4997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 20 1 0 0 0 0 3 4 1 0 0 0 0 3 12 1 0 0 0 0 5 7 1 0 0 0 0 5 13 1 0 0 0 0 6 8 1 0 0 0 0 6 15 1 0 0 0 0 7 19 1 0 0 0 0 8 21 1 0 0 0 0 9 12 1 0 0 0 0 9 13 1 0 0 0 0 10 16 1 0 0 0 0 10 20 1 0 0 0 0 11 17 1 0 0 0 0 11 22 1 0 0 0 0 12 19 1 1 0 0 0 13 23 1 1 0 0 0 14 4 1 1 0 0 0 14 15 1 0 0 0 0 14 18 1 0 0 0 0 15 20 1 6 0 0 0 16 18 1 0 0 0 0 16 24 2 0 0 0 0 17 21 1 0 0 0 0 17 25 1 1 0 0 0 18 19 1 6 0 0 0 19 1 1 6 0 0 0 20 21 1 1 0 0 0 21 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.24
Volume:	378.861
LogP:	1.672
LogD:	1.439
LogS:	-3.321
# Rotatable Bonds:	2
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.596
Synthetic Accessibility Score:	4.673
Fsp3:	0.952
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.984
MDCK Permeability:	9.784370377019513e-06
Pgp-inhibitor:	0.009
Pgp-substrate:	0.976
Human Intestinal Absorption (HIA):	0.107
20% Bioavailability (F20%):	0.14
30% Bioavailability (F30%):	0.153

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.784
Plasma Protein Binding (PPB):	39.06620788574219%
Volume Distribution (VD):	0.872
Pgp-substrate:	39.14537048339844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.684
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.772
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.505
CYP3A4-substrate:	0.206

ADMET: Excretion

Clearance (CL):	6.601
Half-life (T1/2):	0.644

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.429
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.896
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.352
Carcinogencity:	0.859
Eye Corrosion:	0.169
Eye Irritation:	0.129
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC317066

Natural Product ID:	NPC317066
*Common Name:**	5Beta-Pregnan-3A,17A,20Beta,21-Tetrol-11-One
IUPAC Name:	(3R,5R,8S,9S,10S,13S,14S,17R)-17-[(1S)-1,2-dihydroxyethyl]-3,17-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-11-one
Synonyms:
Standard InCHIKey:	JXCOSKURGJMQSG-AZQJGLEESA-N
Standard InCHI:	InChI=1S/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-15,17-18,22-23,25-26H,3-11H2,1-2H3/t12-,13-,14+,15+,17+,18-,19+,20+,21+/m1/s1
SMILES:	OC[C@@H]([C@@]1(O)CC[C@@H]2[C@]1(C)CC(=O)[C@H]1[C@H]2CC[C@H]2[C@]1(C)CC[C@H](C2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1908042
PubChem CID:	160499
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids [CHEMONTID:0003095] 21-hydroxysteroids

*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	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT701	Individual Protein	UDP-glucuronosyltransferase 2B4	Homo sapiens	Activity	=	4.0	total picomoles	PMID[575287]
NPT697	Individual Protein	UDP-glucuronosyltransferase 2B7	Homo sapiens	Activity	=	12.0	total picomoles	PMID[575287]

☑ 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 NPC317066 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	362
0.1-0.2	3233
0.2-0.3	11034
0.3-0.4	12769
0.4-0.5	5840
0.5-0.6	5208
0.6-0.7	3254
0.7-0.8	849
0.8-0.85	88
0.85-0.9	43
0.9-0.95	16
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9231	High Similarity	NPC470609
0.9125	High Similarity	NPC327451
0.9024	High Similarity	NPC476727
0.9024	High Similarity	NPC476726
0.9	High Similarity	NPC328007
0.8961	High Similarity	NPC472487
0.8961	High Similarity	NPC472486
0.8947	High Similarity	NPC472854
0.8846	High Similarity	NPC264602
0.8831	High Similarity	NPC21220
0.8831	High Similarity	NPC125767
0.8795	High Similarity	NPC472272
0.8734	High Similarity	NPC185465
0.869	High Similarity	NPC263802
0.8684	High Similarity	NPC156277
0.8684	High Similarity	NPC58057
0.8684	High Similarity	NPC151018
0.8684	High Similarity	NPC320549
0.8625	High Similarity	NPC320144
0.8608	High Similarity	NPC23884
0.8608	High Similarity	NPC221420
0.8608	High Similarity	NPC180199
0.8608	High Similarity	NPC477919
0.859	High Similarity	NPC24014
0.859	High Similarity	NPC27349
0.8571	High Similarity	NPC232112
0.8571	High Similarity	NPC310766
0.8571	High Similarity	NPC80700
0.8554	High Similarity	NPC50438
0.85	High Similarity	NPC199965
0.85	High Similarity	NPC476732
0.8481	Intermediate Similarity	NPC5767
0.8481	Intermediate Similarity	NPC475742
0.8462	Intermediate Similarity	NPC254340
0.8462	Intermediate Similarity	NPC133922
0.8442	Intermediate Similarity	NPC89310
0.8421	Intermediate Similarity	NPC6120
0.8421	Intermediate Similarity	NPC327728
0.8421	Intermediate Similarity	NPC213178
0.8421	Intermediate Similarity	NPC131892
0.8421	Intermediate Similarity	NPC324607
0.8421	Intermediate Similarity	NPC321732
0.8415	Intermediate Similarity	NPC469745
0.8415	Intermediate Similarity	NPC12933
0.8395	Intermediate Similarity	NPC472310
0.8391	Intermediate Similarity	NPC476296
0.8375	Intermediate Similarity	NPC475031
0.8354	Intermediate Similarity	NPC174964
0.8354	Intermediate Similarity	NPC97534
0.8354	Intermediate Similarity	NPC159789
0.8354	Intermediate Similarity	NPC195155
0.8354	Intermediate Similarity	NPC273366
0.8353	Intermediate Similarity	NPC474448
0.8313	Intermediate Similarity	NPC268040
0.8313	Intermediate Similarity	NPC477935
0.8293	Intermediate Similarity	NPC472853
0.8276	Intermediate Similarity	NPC61688
0.8276	Intermediate Similarity	NPC24705
0.8276	Intermediate Similarity	NPC56962
0.8256	Intermediate Similarity	NPC202937
0.825	Intermediate Similarity	NPC4209
0.8228	Intermediate Similarity	NPC167702
0.8228	Intermediate Similarity	NPC280026
0.8222	Intermediate Similarity	NPC470031
0.8214	Intermediate Similarity	NPC259173
0.8214	Intermediate Similarity	NPC472744
0.8202	Intermediate Similarity	NPC476189
0.8202	Intermediate Similarity	NPC472496
0.8193	Intermediate Similarity	NPC77311
0.8182	Intermediate Similarity	NPC107919
0.8148	Intermediate Similarity	NPC207010
0.8148	Intermediate Similarity	NPC317913
0.814	Intermediate Similarity	NPC92139
0.8125	Intermediate Similarity	NPC317242
0.8125	Intermediate Similarity	NPC212733
0.8111	Intermediate Similarity	NPC470424
0.8111	Intermediate Similarity	NPC470423
0.8101	Intermediate Similarity	NPC153719
0.8101	Intermediate Similarity	NPC81759
0.8095	Intermediate Similarity	NPC61107
0.8095	Intermediate Similarity	NPC289486
0.8095	Intermediate Similarity	NPC30583
0.8095	Intermediate Similarity	NPC121121
0.8095	Intermediate Similarity	NPC477936
0.8049	Intermediate Similarity	NPC34046
0.8049	Intermediate Similarity	NPC224802
0.8049	Intermediate Similarity	NPC80089
0.8049	Intermediate Similarity	NPC324700
0.8049	Intermediate Similarity	NPC171426
0.8046	Intermediate Similarity	NPC472497
0.8025	Intermediate Similarity	NPC163597
0.8	Intermediate Similarity	NPC292458
0.8	Intermediate Similarity	NPC217559
0.8	Intermediate Similarity	NPC268578
0.8	Intermediate Similarity	NPC161035
0.7979	Intermediate Similarity	NPC178853
0.7976	Intermediate Similarity	NPC58631
0.7955	Intermediate Similarity	NPC477614
0.7955	Intermediate Similarity	NPC226491
0.7952	Intermediate Similarity	NPC245029
0.7952	Intermediate Similarity	NPC80891
0.7952	Intermediate Similarity	NPC201276
0.7952	Intermediate Similarity	NPC31302
0.7935	Intermediate Similarity	NPC476728
0.7935	Intermediate Similarity	NPC116683
0.7931	Intermediate Similarity	NPC302111
0.7931	Intermediate Similarity	NPC472745
0.7927	Intermediate Similarity	NPC143133
0.7927	Intermediate Similarity	NPC302578
0.7927	Intermediate Similarity	NPC105208
0.7927	Intermediate Similarity	NPC185915
0.7927	Intermediate Similarity	NPC128951
0.7927	Intermediate Similarity	NPC477227
0.7927	Intermediate Similarity	NPC192046
0.7927	Intermediate Similarity	NPC298168
0.7922	Intermediate Similarity	NPC472984
0.7922	Intermediate Similarity	NPC63190
0.7912	Intermediate Similarity	NPC206878
0.7901	Intermediate Similarity	NPC472311
0.7901	Intermediate Similarity	NPC68565
0.7901	Intermediate Similarity	NPC35871
0.7895	Intermediate Similarity	NPC190827
0.7895	Intermediate Similarity	NPC475943
0.7895	Intermediate Similarity	NPC243469
0.7889	Intermediate Similarity	NPC52756
0.7875	Intermediate Similarity	NPC470610
0.7857	Intermediate Similarity	NPC164999
0.7857	Intermediate Similarity	NPC477851
0.7849	Intermediate Similarity	NPC471241
0.7849	Intermediate Similarity	NPC170978
0.7841	Intermediate Similarity	NPC239938
0.7841	Intermediate Similarity	NPC472495
0.7841	Intermediate Similarity	NPC241875
0.7841	Intermediate Similarity	NPC469317
0.7841	Intermediate Similarity	NPC174619
0.7841	Intermediate Similarity	NPC469314
0.7831	Intermediate Similarity	NPC329117
0.7831	Intermediate Similarity	NPC18857
0.7831	Intermediate Similarity	NPC67657
0.7826	Intermediate Similarity	NPC17336
0.7821	Intermediate Similarity	NPC473225
0.7821	Intermediate Similarity	NPC474954
0.7812	Intermediate Similarity	NPC191892
0.7805	Intermediate Similarity	NPC470145
0.7805	Intermediate Similarity	NPC471046
0.7805	Intermediate Similarity	NPC108840
0.7791	Intermediate Similarity	NPC472498
0.7791	Intermediate Similarity	NPC86370
0.7778	Intermediate Similarity	NPC475056
0.7778	Intermediate Similarity	NPC100313
0.7778	Intermediate Similarity	NPC168511
0.7778	Intermediate Similarity	NPC180849
0.7778	Intermediate Similarity	NPC304499
0.7778	Intermediate Similarity	NPC46758
0.7778	Intermediate Similarity	NPC159325
0.7778	Intermediate Similarity	NPC48795
0.7778	Intermediate Similarity	NPC477930
0.7778	Intermediate Similarity	NPC77756
0.7766	Intermediate Similarity	NPC476294
0.7765	Intermediate Similarity	NPC254123
0.7763	Intermediate Similarity	NPC159654
0.7763	Intermediate Similarity	NPC167995
0.7763	Intermediate Similarity	NPC281540
0.7763	Intermediate Similarity	NPC118937
0.775	Intermediate Similarity	NPC126642
0.775	Intermediate Similarity	NPC473267
0.7742	Intermediate Similarity	NPC49371
0.7738	Intermediate Similarity	NPC287452
0.7738	Intermediate Similarity	NPC52951
0.7732	Intermediate Similarity	NPC100078
0.7722	Intermediate Similarity	NPC470830
0.7722	Intermediate Similarity	NPC476734
0.7722	Intermediate Similarity	NPC469941
0.7722	Intermediate Similarity	NPC319671
0.7722	Intermediate Similarity	NPC299948
0.7722	Intermediate Similarity	NPC252032
0.7722	Intermediate Similarity	NPC241085
0.7717	Intermediate Similarity	NPC477495
0.7717	Intermediate Similarity	NPC280804
0.7711	Intermediate Similarity	NPC477918
0.7711	Intermediate Similarity	NPC474404
0.7711	Intermediate Similarity	NPC171658
0.7708	Intermediate Similarity	NPC477915
0.7708	Intermediate Similarity	NPC213528
0.7708	Intermediate Similarity	NPC470172
0.7708	Intermediate Similarity	NPC244969
0.7701	Intermediate Similarity	NPC25037
0.7701	Intermediate Similarity	NPC146683
0.7701	Intermediate Similarity	NPC474996
0.7701	Intermediate Similarity	NPC473336
0.7701	Intermediate Similarity	NPC471044
0.7701	Intermediate Similarity	NPC105895
0.7701	Intermediate Similarity	NPC474482
0.7701	Intermediate Similarity	NPC34984
0.7701	Intermediate Similarity	NPC319909
0.7701	Intermediate Similarity	NPC475745
0.7684	Intermediate Similarity	NPC20028
0.7683	Intermediate Similarity	NPC196136
0.7683	Intermediate Similarity	NPC158208
0.7683	Intermediate Similarity	NPC243027

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 NPC317066 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	388
0.1-0.2	3632
0.2-0.3	3513
0.3-0.4	977
0.4-0.5	240
0.5-0.6	193
0.6-0.7	150
0.7-0.8	37
0.8-0.85	12
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8684	High Similarity	NPD4808	Clinical (unspecified phase)
0.8684	High Similarity	NPD4809	Clinical (unspecified phase)
0.8553	High Similarity	NPD4245	Approved
0.8553	High Similarity	NPD4244	Approved
0.8421	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD3698	Phase 2
0.8354	Intermediate Similarity	NPD3703	Phase 2
0.8289	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD5360	Phase 3
0.825	Intermediate Similarity	NPD6117	Approved
0.8228	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD6116	Phase 1
0.8077	Intermediate Similarity	NPD4789	Approved
0.8049	Intermediate Similarity	NPD6697	Approved
0.8049	Intermediate Similarity	NPD6115	Approved
0.8049	Intermediate Similarity	NPD6118	Approved
0.8049	Intermediate Similarity	NPD6114	Approved
0.7895	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD4758	Discontinued
0.7683	Intermediate Similarity	NPD3702	Approved
0.7625	Intermediate Similarity	NPD4787	Phase 1
0.7619	Intermediate Similarity	NPD3671	Phase 1
0.7619	Intermediate Similarity	NPD5364	Discontinued
0.7586	Intermediate Similarity	NPD4788	Approved
0.7551	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD5777	Approved
0.7531	Intermediate Similarity	NPD6081	Approved
0.7474	Intermediate Similarity	NPD4755	Approved
0.7342	Intermediate Similarity	NPD4224	Phase 2
0.732	Intermediate Similarity	NPD5285	Approved
0.732	Intermediate Similarity	NPD5286	Approved
0.732	Intermediate Similarity	NPD4700	Approved
0.732	Intermediate Similarity	NPD4696	Approved
0.7283	Intermediate Similarity	NPD5328	Approved
0.7222	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4633	Approved
0.7172	Intermediate Similarity	NPD5226	Approved
0.7172	Intermediate Similarity	NPD5224	Approved
0.7172	Intermediate Similarity	NPD5211	Phase 2
0.7172	Intermediate Similarity	NPD5225	Approved
0.7129	Intermediate Similarity	NPD5739	Approved
0.7129	Intermediate Similarity	NPD6402	Approved
0.7129	Intermediate Similarity	NPD6675	Approved
0.7129	Intermediate Similarity	NPD7128	Approved
0.7128	Intermediate Similarity	NPD6079	Approved
0.7111	Intermediate Similarity	NPD4786	Approved
0.71	Intermediate Similarity	NPD5174	Approved
0.71	Intermediate Similarity	NPD5175	Approved
0.7097	Intermediate Similarity	NPD4753	Phase 2
0.7087	Intermediate Similarity	NPD6372	Approved
0.7087	Intermediate Similarity	NPD6373	Approved
0.7071	Intermediate Similarity	NPD5223	Approved
0.7053	Intermediate Similarity	NPD4202	Approved
0.703	Intermediate Similarity	NPD5141	Approved
0.7019	Intermediate Similarity	NPD4634	Approved
0.701	Intermediate Similarity	NPD4697	Phase 3
0.699	Remote Similarity	NPD6881	Approved
0.699	Remote Similarity	NPD7320	Approved
0.699	Remote Similarity	NPD6899	Approved
0.6961	Remote Similarity	NPD4767	Approved
0.6961	Remote Similarity	NPD4768	Approved
0.6957	Remote Similarity	NPD3618	Phase 1
0.6952	Remote Similarity	NPD6650	Approved
0.6952	Remote Similarity	NPD6649	Approved
0.6947	Remote Similarity	NPD8034	Phase 2
0.6947	Remote Similarity	NPD8035	Phase 2
0.6931	Remote Similarity	NPD4754	Approved
0.6923	Remote Similarity	NPD3133	Approved
0.6923	Remote Similarity	NPD3666	Approved
0.6923	Remote Similarity	NPD3665	Phase 1
0.6907	Remote Similarity	NPD4629	Approved
0.6907	Remote Similarity	NPD5210	Approved
0.6893	Remote Similarity	NPD5701	Approved
0.6893	Remote Similarity	NPD5697	Approved
0.6889	Remote Similarity	NPD3667	Approved
0.6887	Remote Similarity	NPD8297	Approved
0.6857	Remote Similarity	NPD6883	Approved
0.6857	Remote Similarity	NPD7102	Approved
0.6857	Remote Similarity	NPD7290	Approved
0.6837	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5221	Approved
0.6837	Remote Similarity	NPD5222	Approved
0.6827	Remote Similarity	NPD4729	Approved
0.6827	Remote Similarity	NPD5128	Approved
0.6827	Remote Similarity	NPD4730	Approved
0.6792	Remote Similarity	NPD6617	Approved
0.6792	Remote Similarity	NPD6869	Approved
0.6792	Remote Similarity	NPD8130	Phase 1
0.6792	Remote Similarity	NPD6847	Approved
0.6768	Remote Similarity	NPD5173	Approved
0.6768	Remote Similarity	NPD6084	Phase 2
0.6768	Remote Similarity	NPD6083	Phase 2
0.6762	Remote Similarity	NPD6014	Approved
0.6762	Remote Similarity	NPD6013	Approved
0.6762	Remote Similarity	NPD6012	Approved
0.6729	Remote Similarity	NPD6882	Approved
0.6703	Remote Similarity	NPD4223	Phase 3
0.6703	Remote Similarity	NPD4221	Approved
0.6701	Remote Similarity	NPD6399	Phase 3
0.6698	Remote Similarity	NPD5249	Phase 3
0.6698	Remote Similarity	NPD5247	Approved
0.6698	Remote Similarity	NPD5250	Approved
0.6698	Remote Similarity	NPD5251	Approved
0.6698	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD7525	Registered
0.6667	Remote Similarity	NPD6928	Phase 2
0.6667	Remote Similarity	NPD4632	Approved
0.6636	Remote Similarity	NPD5215	Approved
0.6636	Remote Similarity	NPD5216	Approved
0.6636	Remote Similarity	NPD5217	Approved
0.6636	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4692	Approved
0.6593	Remote Similarity	NPD4139	Approved
0.6582	Remote Similarity	NPD3198	Approved
0.6569	Remote Similarity	NPD1700	Approved
0.6559	Remote Similarity	NPD4197	Approved
0.6542	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5135	Approved
0.6542	Remote Similarity	NPD5169	Approved
0.6535	Remote Similarity	NPD5696	Approved
0.6531	Remote Similarity	NPD8171	Discontinued
0.6509	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5127	Approved
0.6476	Remote Similarity	NPD6920	Discontinued
0.6471	Remote Similarity	NPD8418	Phase 2
0.646	Remote Similarity	NPD6059	Approved
0.646	Remote Similarity	NPD6054	Approved
0.646	Remote Similarity	NPD6319	Approved
0.6429	Remote Similarity	NPD7515	Phase 2
0.6421	Remote Similarity	NPD4689	Approved
0.6421	Remote Similarity	NPD4688	Approved
0.6421	Remote Similarity	NPD4693	Phase 3
0.6421	Remote Similarity	NPD4690	Approved
0.6421	Remote Similarity	NPD4138	Approved
0.6421	Remote Similarity	NPD5205	Approved
0.6415	Remote Similarity	NPD6412	Phase 2
0.64	Remote Similarity	NPD5695	Phase 3
0.6396	Remote Similarity	NPD6274	Approved
0.6383	Remote Similarity	NPD3668	Phase 3
0.6372	Remote Similarity	NPD7100	Approved
0.6372	Remote Similarity	NPD7101	Approved
0.6364	Remote Similarity	NPD8133	Approved
0.6348	Remote Similarity	NPD6370	Approved
0.6339	Remote Similarity	NPD6009	Approved
0.6339	Remote Similarity	NPD7115	Discovery
0.6325	Remote Similarity	NPD7507	Approved
0.6321	Remote Similarity	NPD6008	Approved
0.6306	Remote Similarity	NPD5167	Approved
0.6304	Remote Similarity	NPD4748	Discontinued
0.6289	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6335	Approved
0.6264	Remote Similarity	NPD3617	Approved
0.6263	Remote Similarity	NPD5281	Approved
0.6263	Remote Similarity	NPD5284	Approved
0.6261	Remote Similarity	NPD6016	Approved
0.6261	Remote Similarity	NPD6015	Approved
0.6261	Remote Similarity	NPD6908	Approved
0.6261	Remote Similarity	NPD6909	Approved
0.625	Remote Similarity	NPD5280	Approved
0.625	Remote Similarity	NPD6409	Approved
0.625	Remote Similarity	NPD5279	Phase 3
0.625	Remote Similarity	NPD5330	Approved
0.625	Remote Similarity	NPD6684	Approved
0.625	Remote Similarity	NPD5690	Phase 2
0.625	Remote Similarity	NPD7334	Approved
0.625	Remote Similarity	NPD4694	Approved
0.625	Remote Similarity	NPD7146	Approved
0.625	Remote Similarity	NPD7521	Approved
0.6239	Remote Similarity	NPD7492	Approved
0.6238	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD7736	Approved
0.6214	Remote Similarity	NPD7638	Approved
0.6207	Remote Similarity	NPD5988	Approved
0.6204	Remote Similarity	NPD5168	Approved
0.6195	Remote Similarity	NPD6317	Approved
0.6186	Remote Similarity	NPD6616	Approved
0.6167	Remote Similarity	NPD7319	Approved
0.6154	Remote Similarity	NPD7640	Approved
0.6154	Remote Similarity	NPD7604	Phase 2
0.6154	Remote Similarity	NPD7639	Approved
0.614	Remote Similarity	NPD6313	Approved
0.614	Remote Similarity	NPD6314	Approved
0.6139	Remote Similarity	NPD7748	Approved
0.6134	Remote Similarity	NPD7078	Approved
0.6134	Remote Similarity	NPD8293	Discontinued
0.6129	Remote Similarity	NPD5368	Approved
0.6122	Remote Similarity	NPD6903	Approved
0.6121	Remote Similarity	NPD5983	Phase 2
0.6121	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD7902	Approved
0.6111	Remote Similarity	NPD6942	Approved
0.6111	Remote Similarity	NPD7339	Approved
0.6106	Remote Similarity	NPD6940	Discontinued
0.6087	Remote Similarity	NPD4802	Phase 2

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