NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	710.39
Volume:	697.613
LogP:	2.788
LogD:	2.43
LogS:	-4.399
# Rotatable Bonds:	9
TPSA:	171.97
# H-Bond Aceptor:	13
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.191
Synthetic Accessibility Score:	6.665
Fsp3:	0.946
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.469
MDCK Permeability:	0.0001310822699451819
Pgp-inhibitor:	0.234
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.163

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	42.529693603515625%
Volume Distribution (VD):	0.666
Pgp-substrate:	25.04461097717285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.985
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.736
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.1
CYP3A4-inhibitor:	0.272
CYP3A4-substrate:	0.818

ADMET: Excretion

Clearance (CL):	4.105
Half-life (T1/2):	0.488

ADMET: Toxicity

hERG Blockers:	0.885
Human Hepatotoxicity (H-HT):	0.343
Drug-inuced Liver Injury (DILI):	0.521
AMES Toxicity:	0.129
Rat Oral Acute Toxicity:	0.762
Maximum Recommended Daily Dose:	0.052
Skin Sensitization:	0.584
Carcinogencity:	0.25
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC477489

Natural Product ID:	NPC477489
*Common Name:**	[(1S,3R,6S,7S,8S,9S,10S,11S,14S,16S)-6-acetyl-14-[(2R,4R,5R,6R)-5-[(2S,3R,4R,5R,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-8-hydroxy-7,11-dimethyl-2-oxapentacyclo[8.8.0.01,3.03,7.011,16]octadecan-9-yl] acetate
IUPAC Name:	[(1S,3R,6S,7S,8S,9S,10S,11S,14S,16S)-6-acetyl-14-[(2R,4R,5R,6R)-5-[(2S,3R,4R,5R,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-8-hydroxy-7,11-dimethyl-2-oxapentacyclo[8.8.0.01,3.03,7.011,16]octadecan-9-yl] acetate
Synonyms:
Standard InCHIKey:	ITXVKLFFCLEGHM-SEGGQGBKSA-N
Standard InCHI:	InChI=1S/C37H58O13/c1-17(38)23-11-14-37-35(23,6)32(42)30(47-20(4)39)31-34(5)12-10-22(15-21(34)9-13-36(31,37)50-37)48-25-16-24(43-7)28(19(3)45-25)49-33-27(41)29(44-8)26(40)18(2)46-33/h18-19,21-33,40-42H,9-16H2,1-8H3/t18-,19-,21+,22+,23-,24-,25+,26-,27-,28-,29-,30+,31-,32-,33+,34+,35+,36+,37-/m1/s1
SMILES:	C[C@@H]1[C@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H](C[C@H]2OC)O[C@H]3CC[C@]4([C@H](C3)CC[C@]56[C@@H]4[C@@H]([C@H]([C@]7([C@]5(O6)CC[C@@H]7C(=O)C)C)O)OC(=O)C)C)C)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118724166
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001691] Steroid esters

*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
NPO23320	Marsdenia tenacissima	Species	Apocynaceae	Eukaryota	stems	Simao County, Yunnan Province, China	2005-MAR	PMID[25215856]
NPO23320	Marsdenia tenacissima	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23320	Marsdenia tenacissima	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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
IC50	2
Others	1

Activity Type	# Activity
Others	3

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Ratio IC50	=	130	n.a.	PMID[25215856]
NPT2	Others	Unspecified	IC50	=	180	nM	PMID[25215856]
NPT2	Others	Unspecified	IC50	=	23400	nM	PMID[25215856]

☑ 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 NPC477489 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	611
0.1-0.2	4227
0.2-0.3	9467
0.3-0.4	12510
0.4-0.5	6848
0.5-0.6	4514
0.6-0.7	2665
0.7-0.8	1630
0.8-0.85	123
0.85-0.9	92
0.9-0.95	8
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9619	High Similarity	NPC477492
0.9223	High Similarity	NPC34562
0.8981	High Similarity	NPC469824
0.8972	High Similarity	NPC227879
0.8972	High Similarity	NPC208333
0.8962	High Similarity	NPC203974
0.8952	High Similarity	NPC470167
0.8932	High Similarity	NPC20028
0.8879	High Similarity	NPC472079
0.8868	High Similarity	NPC215408
0.8857	High Similarity	NPC471253
0.8857	High Similarity	NPC107385
0.8857	High Similarity	NPC473406
0.8846	High Similarity	NPC477172
0.8818	High Similarity	NPC97002
0.8803	High Similarity	NPC114306
0.8803	High Similarity	NPC477490
0.8796	High Similarity	NPC236753
0.8796	High Similarity	NPC228190
0.8762	High Similarity	NPC470172
0.8762	High Similarity	NPC80191
0.8762	High Similarity	NPC471254
0.8762	High Similarity	NPC310031
0.875	High Similarity	NPC41843
0.8739	High Similarity	NPC79193
0.8738	High Similarity	NPC472273
0.8704	High Similarity	NPC202898
0.8704	High Similarity	NPC469826
0.8704	High Similarity	NPC475319
0.8704	High Similarity	NPC92890
0.8655	High Similarity	NPC477493
0.8641	High Similarity	NPC296936
0.8636	High Similarity	NPC473062
0.8624	High Similarity	NPC233433
0.8624	High Similarity	NPC220836
0.8624	High Similarity	NPC92297
0.8624	High Similarity	NPC94086
0.8624	High Similarity	NPC273002
0.8624	High Similarity	NPC473817
0.8584	High Similarity	NPC179429
0.8558	High Similarity	NPC471241
0.8544	High Similarity	NPC57964
0.8544	High Similarity	NPC94582
0.8544	High Similarity	NPC215570
0.8505	High Similarity	NPC476837
0.8505	High Similarity	NPC139181
0.8505	High Similarity	NPC97260
0.8491	Intermediate Similarity	NPC476839
0.8491	Intermediate Similarity	NPC108227
0.8491	Intermediate Similarity	NPC472081
0.8491	Intermediate Similarity	NPC475574
0.8491	Intermediate Similarity	NPC476838
0.8491	Intermediate Similarity	NPC476512
0.8455	Intermediate Similarity	NPC469825
0.8447	Intermediate Similarity	NPC477495
0.844	Intermediate Similarity	NPC126753
0.8426	Intermediate Similarity	NPC469827
0.8411	Intermediate Similarity	NPC310138
0.8411	Intermediate Similarity	NPC470029
0.8411	Intermediate Similarity	NPC114700
0.8411	Intermediate Similarity	NPC134967
0.8381	Intermediate Similarity	NPC470591
0.8378	Intermediate Similarity	NPC470622
0.8365	Intermediate Similarity	NPC92196
0.8349	Intermediate Similarity	NPC306776
0.8349	Intermediate Similarity	NPC166079
0.8286	Intermediate Similarity	NPC203434
0.8286	Intermediate Similarity	NPC252056
0.8286	Intermediate Similarity	NPC238796
0.8286	Intermediate Similarity	NPC237071
0.8269	Intermediate Similarity	NPC309866
0.8269	Intermediate Similarity	NPC191915
0.8269	Intermediate Similarity	NPC151214
0.8257	Intermediate Similarity	NPC100078
0.8252	Intermediate Similarity	NPC204881
0.8252	Intermediate Similarity	NPC473830
0.8252	Intermediate Similarity	NPC293609
0.8241	Intermediate Similarity	NPC80640
0.823	Intermediate Similarity	NPC157571
0.823	Intermediate Similarity	NPC207845
0.823	Intermediate Similarity	NPC472719
0.8224	Intermediate Similarity	NPC470030
0.8214	Intermediate Similarity	NPC471431
0.8208	Intermediate Similarity	NPC477222
0.8208	Intermediate Similarity	NPC210157
0.8208	Intermediate Similarity	NPC477223
0.8208	Intermediate Similarity	NPC266417
0.8198	Intermediate Similarity	NPC207693
0.819	Intermediate Similarity	NPC477494
0.8182	Intermediate Similarity	NPC158051
0.8182	Intermediate Similarity	NPC119628
0.8182	Intermediate Similarity	NPC158367
0.8174	Intermediate Similarity	NPC475490
0.8173	Intermediate Similarity	NPC277774
0.8173	Intermediate Similarity	NPC473726
0.8155	Intermediate Similarity	NPC279329
0.8155	Intermediate Similarity	NPC65550
0.8148	Intermediate Similarity	NPC178853
0.8142	Intermediate Similarity	NPC274833
0.813	Intermediate Similarity	NPC473805
0.813	Intermediate Similarity	NPC473519
0.8125	Intermediate Similarity	NPC240125
0.8125	Intermediate Similarity	NPC22709
0.8125	Intermediate Similarity	NPC87393
0.8125	Intermediate Similarity	NPC91583
0.8125	Intermediate Similarity	NPC51947
0.8125	Intermediate Similarity	NPC473844
0.8113	Intermediate Similarity	NPC163685
0.8113	Intermediate Similarity	NPC475765
0.8113	Intermediate Similarity	NPC235109
0.8113	Intermediate Similarity	NPC142264
0.8113	Intermediate Similarity	NPC476510
0.8113	Intermediate Similarity	NPC475785
0.8108	Intermediate Similarity	NPC475630
0.8108	Intermediate Similarity	NPC138219
0.8108	Intermediate Similarity	NPC40716
0.8108	Intermediate Similarity	NPC475234
0.8103	Intermediate Similarity	NPC477252
0.8103	Intermediate Similarity	NPC473304
0.8095	Intermediate Similarity	NPC473774
0.8095	Intermediate Similarity	NPC3538
0.8095	Intermediate Similarity	NPC24960
0.8095	Intermediate Similarity	NPC113500
0.8095	Intermediate Similarity	NPC252253
0.8095	Intermediate Similarity	NPC45959
0.8095	Intermediate Similarity	NPC477224
0.8091	Intermediate Similarity	NPC88469
0.8091	Intermediate Similarity	NPC267637
0.8091	Intermediate Similarity	NPC327093
0.8087	Intermediate Similarity	NPC477465
0.8077	Intermediate Similarity	NPC36372
0.8073	Intermediate Similarity	NPC213528
0.8073	Intermediate Similarity	NPC244969
0.8065	Intermediate Similarity	NPC102015
0.8058	Intermediate Similarity	NPC131466
0.8058	Intermediate Similarity	NPC473472
0.8056	Intermediate Similarity	NPC80417
0.8053	Intermediate Similarity	NPC66513
0.8037	Intermediate Similarity	NPC233649
0.8037	Intermediate Similarity	NPC470028
0.8036	Intermediate Similarity	NPC262567
0.8036	Intermediate Similarity	NPC231566
0.8036	Intermediate Similarity	NPC473688
0.8036	Intermediate Similarity	NPC471626
0.8036	Intermediate Similarity	NPC88744
0.8019	Intermediate Similarity	NPC82633
0.8018	Intermediate Similarity	NPC184805
0.8018	Intermediate Similarity	NPC273189
0.8017	Intermediate Similarity	NPC472718
0.8017	Intermediate Similarity	NPC88945
0.8	Intermediate Similarity	NPC144790
0.8	Intermediate Similarity	NPC102619
0.8	Intermediate Similarity	NPC172838
0.8	Intermediate Similarity	NPC311246
0.8	Intermediate Similarity	NPC167644
0.8	Intermediate Similarity	NPC161035
0.8	Intermediate Similarity	NPC88962
0.8	Intermediate Similarity	NPC149400
0.8	Intermediate Similarity	NPC137004
0.7982	Intermediate Similarity	NPC11035
0.7982	Intermediate Similarity	NPC204392
0.7982	Intermediate Similarity	NPC275668
0.7982	Intermediate Similarity	NPC240734
0.7982	Intermediate Similarity	NPC91838
0.7982	Intermediate Similarity	NPC1876
0.7981	Intermediate Similarity	NPC77756
0.7981	Intermediate Similarity	NPC223143
0.7965	Intermediate Similarity	NPC8431
0.7963	Intermediate Similarity	NPC472144
0.7961	Intermediate Similarity	NPC281004
0.7961	Intermediate Similarity	NPC476379
0.7949	Intermediate Similarity	NPC78836
0.7949	Intermediate Similarity	NPC156651
0.7946	Intermediate Similarity	NPC471430
0.7944	Intermediate Similarity	NPC121453
0.7944	Intermediate Similarity	NPC473287
0.7944	Intermediate Similarity	NPC116683
0.7944	Intermediate Similarity	NPC476728
0.7944	Intermediate Similarity	NPC156377
0.7944	Intermediate Similarity	NPC304011
0.7944	Intermediate Similarity	NPC139271
0.7931	Intermediate Similarity	NPC470115
0.7931	Intermediate Similarity	NPC470116
0.7925	Intermediate Similarity	NPC312678
0.7925	Intermediate Similarity	NPC174024
0.7925	Intermediate Similarity	NPC253268
0.7925	Intermediate Similarity	NPC175
0.7925	Intermediate Similarity	NPC294686
0.7925	Intermediate Similarity	NPC222731
0.7925	Intermediate Similarity	NPC473851
0.7925	Intermediate Similarity	NPC179859
0.7925	Intermediate Similarity	NPC291547
0.7925	Intermediate Similarity	NPC475436
0.7925	Intermediate Similarity	NPC473503
0.7925	Intermediate Similarity	NPC131693
0.7925	Intermediate Similarity	NPC470423
0.7913	Intermediate Similarity	NPC470543
0.7913	Intermediate Similarity	NPC477253
0.7913	Intermediate Similarity	NPC243572
0.7905	Intermediate Similarity	NPC5632

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 NPC477489 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	648
0.1-0.2	4062
0.2-0.3	3006
0.3-0.4	785
0.4-0.5	338
0.5-0.6	209
0.6-0.7	83
0.7-0.8	18
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8774	High Similarity	NPD8170	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD8133	Approved
0.783	Intermediate Similarity	NPD8171	Discontinued
0.7652	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7507	Approved
0.7402	Intermediate Similarity	NPD7319	Approved
0.7345	Intermediate Similarity	NPD1700	Approved
0.728	Intermediate Similarity	NPD8328	Phase 3
0.7258	Intermediate Similarity	NPD8380	Approved
0.7258	Intermediate Similarity	NPD8296	Approved
0.7258	Intermediate Similarity	NPD8335	Approved
0.7258	Intermediate Similarity	NPD8378	Approved
0.7258	Intermediate Similarity	NPD8379	Approved
0.7236	Intermediate Similarity	NPD7516	Approved
0.7188	Intermediate Similarity	NPD7736	Approved
0.7177	Intermediate Similarity	NPD8294	Approved
0.7177	Intermediate Similarity	NPD8377	Approved
0.7154	Intermediate Similarity	NPD7328	Approved
0.7154	Intermediate Similarity	NPD7327	Approved
0.712	Intermediate Similarity	NPD8033	Approved
0.7119	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6412	Phase 2
0.6992	Remote Similarity	NPD6940	Discontinued
0.699	Remote Similarity	NPD6114	Approved
0.699	Remote Similarity	NPD6118	Approved
0.699	Remote Similarity	NPD6697	Approved
0.699	Remote Similarity	NPD6115	Approved
0.6977	Remote Similarity	NPD8293	Discontinued
0.6893	Remote Similarity	NPD6116	Phase 1
0.6857	Remote Similarity	NPD6928	Phase 2
0.6822	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD3669	Approved
0.6797	Remote Similarity	NPD6370	Approved
0.6796	Remote Similarity	NPD6117	Approved
0.6792	Remote Similarity	NPD1780	Approved
0.6792	Remote Similarity	NPD1779	Approved
0.6748	Remote Similarity	NPD6882	Approved
0.6748	Remote Similarity	NPD8297	Approved
0.6699	Remote Similarity	NPD3702	Approved
0.6699	Remote Similarity	NPD3703	Phase 2
0.6692	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD6009	Approved
0.6641	Remote Similarity	NPD6059	Approved
0.6641	Remote Similarity	NPD6616	Approved
0.6641	Remote Similarity	NPD6319	Approved
0.6641	Remote Similarity	NPD6054	Approved
0.6639	Remote Similarity	NPD6372	Approved
0.6639	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6373	Approved
0.6637	Remote Similarity	NPD8034	Phase 2
0.6637	Remote Similarity	NPD8035	Phase 2
0.6602	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7078	Approved
0.6589	Remote Similarity	NPD7503	Approved
0.6589	Remote Similarity	NPD6921	Approved
0.6585	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.656	Remote Similarity	NPD4632	Approved
0.6532	Remote Similarity	NPD6650	Approved
0.6532	Remote Similarity	NPD6649	Approved
0.6529	Remote Similarity	NPD6402	Approved
0.6529	Remote Similarity	NPD5739	Approved
0.6529	Remote Similarity	NPD7128	Approved
0.6529	Remote Similarity	NPD6008	Approved
0.6529	Remote Similarity	NPD6675	Approved
0.6462	Remote Similarity	NPD6016	Approved
0.6462	Remote Similarity	NPD8517	Approved
0.6462	Remote Similarity	NPD8516	Approved
0.6462	Remote Similarity	NPD8515	Approved
0.6462	Remote Similarity	NPD8513	Phase 3
0.6462	Remote Similarity	NPD6015	Approved
0.6423	Remote Similarity	NPD7320	Approved
0.6423	Remote Similarity	NPD6881	Approved
0.6423	Remote Similarity	NPD6899	Approved
0.6423	Remote Similarity	NPD6686	Approved
0.6417	Remote Similarity	NPD8086	Approved
0.6417	Remote Similarity	NPD8138	Approved
0.6417	Remote Similarity	NPD8082	Approved
0.6417	Remote Similarity	NPD8083	Approved
0.6417	Remote Similarity	NPD8085	Approved
0.6417	Remote Similarity	NPD8139	Approved
0.6417	Remote Similarity	NPD8084	Approved
0.6412	Remote Similarity	NPD5988	Approved
0.6408	Remote Similarity	NPD5777	Approved
0.6408	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.64	Remote Similarity	NPD8130	Phase 1
0.6364	Remote Similarity	NPD7604	Phase 2
0.6364	Remote Similarity	NPD8275	Approved
0.6364	Remote Similarity	NPD8276	Approved
0.6341	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD5701	Approved
0.6341	Remote Similarity	NPD5697	Approved
0.632	Remote Similarity	NPD7290	Approved
0.632	Remote Similarity	NPD6883	Approved
0.632	Remote Similarity	NPD7102	Approved
0.6311	Remote Similarity	NPD4244	Approved
0.6311	Remote Similarity	NPD8081	Approved
0.6311	Remote Similarity	NPD4245	Approved
0.6311	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD7115	Discovery
0.627	Remote Similarity	NPD6847	Approved
0.627	Remote Similarity	NPD6617	Approved
0.627	Remote Similarity	NPD6869	Approved
0.626	Remote Similarity	NPD8393	Approved
0.625	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.624	Remote Similarity	NPD6012	Approved
0.624	Remote Similarity	NPD6014	Approved
0.624	Remote Similarity	NPD6013	Approved
0.6214	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD3698	Phase 2
0.6214	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD5983	Phase 2
0.6186	Remote Similarity	NPD7991	Discontinued
0.6176	Remote Similarity	NPD6033	Approved
0.616	Remote Similarity	NPD6011	Approved
0.6148	Remote Similarity	NPD6336	Discontinued
0.6142	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD1811	Approved
0.6132	Remote Similarity	NPD1810	Approved
0.6119	Remote Similarity	NPD6067	Discontinued
0.6117	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5360	Phase 3
0.6095	Remote Similarity	NPD6081	Approved
0.6083	Remote Similarity	NPD7902	Approved
0.6083	Remote Similarity	NPD4755	Approved
0.6063	Remote Similarity	NPD4634	Approved
0.6055	Remote Similarity	NPD4238	Approved
0.6055	Remote Similarity	NPD4802	Phase 2
0.6033	Remote Similarity	NPD7638	Approved
0.6017	Remote Similarity	NPD6399	Phase 3
0.6	Remote Similarity	NPD4789	Approved
0.5984	Remote Similarity	NPD5285	Approved
0.5984	Remote Similarity	NPD7639	Approved
0.5984	Remote Similarity	NPD8418	Phase 2
0.5984	Remote Similarity	NPD7640	Approved
0.5984	Remote Similarity	NPD4700	Approved
0.5984	Remote Similarity	NPD4696	Approved
0.5984	Remote Similarity	NPD5286	Approved
0.5966	Remote Similarity	NPD7748	Approved
0.5954	Remote Similarity	NPD6274	Approved
0.5952	Remote Similarity	NPD8140	Approved
0.5952	Remote Similarity	NPD8307	Discontinued
0.595	Remote Similarity	NPD6083	Phase 2
0.595	Remote Similarity	NPD6084	Phase 2
0.594	Remote Similarity	NPD7100	Approved
0.594	Remote Similarity	NPD7101	Approved
0.5922	Remote Similarity	NPD4224	Phase 2
0.5906	Remote Similarity	NPD7625	Phase 1
0.5891	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD7632	Discontinued
0.5887	Remote Similarity	NPD8301	Approved
0.5887	Remote Similarity	NPD5225	Approved
0.5887	Remote Similarity	NPD5224	Approved
0.5887	Remote Similarity	NPD5226	Approved
0.5887	Remote Similarity	NPD4633	Approved
0.5887	Remote Similarity	NPD5211	Phase 2
0.5887	Remote Similarity	NPD8300	Approved
0.5873	Remote Similarity	NPD4767	Approved
0.5873	Remote Similarity	NPD4768	Approved
0.5865	Remote Similarity	NPD6335	Approved
0.5859	Remote Similarity	NPD8306	Approved
0.5859	Remote Similarity	NPD8305	Approved
0.5856	Remote Similarity	NPD7329	Approved
0.5852	Remote Similarity	NPD6909	Approved
0.5852	Remote Similarity	NPD6908	Approved
0.5849	Remote Similarity	NPD2254	Approved
0.5849	Remote Similarity	NPD2687	Approved
0.5849	Remote Similarity	NPD2686	Approved
0.584	Remote Similarity	NPD5175	Approved
0.584	Remote Similarity	NPD5174	Approved
0.5833	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7900	Approved
0.5825	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD8087	Discontinued
0.5806	Remote Similarity	NPD5223	Approved
0.5798	Remote Similarity	NPD7515	Phase 2
0.5794	Remote Similarity	NPD4758	Discontinued
0.5794	Remote Similarity	NPD5141	Approved
0.5789	Remote Similarity	NPD4788	Approved
0.5789	Remote Similarity	NPD6317	Approved
0.5785	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD4729	Approved
0.5781	Remote Similarity	NPD4730	Approved
0.5781	Remote Similarity	NPD8174	Phase 2
0.5775	Remote Similarity	NPD8338	Approved
0.5772	Remote Similarity	NPD5696	Approved
0.5766	Remote Similarity	NPD5364	Discontinued
0.5766	Remote Similarity	NPD3671	Phase 1
0.5763	Remote Similarity	NPD5328	Approved
0.5755	Remote Similarity	NPD8074	Phase 3
0.575	Remote Similarity	NPD4202	Approved
0.5746	Remote Similarity	NPD6313	Approved
0.5746	Remote Similarity	NPD6314	Approved
0.5735	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD371	Approved
0.5714	Remote Similarity	NPD4754	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