NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	830.43
Volume:	796.038
LogP:	1.415
LogD:	1.802
LogS:	-3.624
# Rotatable Bonds:	10
TPSA:	245.05
# H-Bond Aceptor:	17
# H-Bond Donor:	7
# Rings:	8
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.11
Synthetic Accessibility Score:	7.029
Fsp3:	0.976
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.291
MDCK Permeability:	0.00020913223852403462
Pgp-inhibitor:	0.53
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.673
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.68

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.101
Plasma Protein Binding (PPB):	39.1024055480957%
Volume Distribution (VD):	0.273
Pgp-substrate:	23.66793441772461%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.993
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.425
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.041
CYP3A4-substrate:	0.161

ADMET: Excretion

Clearance (CL):	1.28
Half-life (T1/2):	0.748

ADMET: Toxicity

hERG Blockers:	0.461
Human Hepatotoxicity (H-HT):	0.216
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.103
Rat Oral Acute Toxicity:	0.281
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.77
Carcinogencity:	0.228
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC477492

Natural Product ID:	NPC477492
*Common Name:**	1-[(1S,3R,6S,7S,8S,9S,10S,11S,14S,16S)-8,9-dihydroxy-14-[(2R,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-3-hydroxy-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-7,11-dimethyl-2-oxapentacyclo[8.8.0.01,3.03,7.011,16]octadecan-6-yl]ethanone
IUPAC Name:	1-[(1S,3R,6S,7S,8S,9S,10S,11S,14S,16S)-8,9-dihydroxy-14-[(2R,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-3-hydroxy-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-7,11-dimethyl-2-oxapentacyclo[8.8.0.01,3.03,7.011,16]octadecan-6-yl]ethanone
Synonyms:
Standard InCHIKey:	YJEXOKKVHFUILN-QTHQHZGVSA-N
Standard InCHI:	InChI=1S/C41H66O17/c1-17(43)22-10-13-41-39(22,5)35(49)30(48)34-38(4)11-9-21(14-20(38)8-12-40(34,41)58-41)54-25-15-23(50-6)31(18(2)52-25)56-37-29(47)33(51-7)32(19(3)53-37)57-36-28(46)27(45)26(44)24(16-42)55-36/h18-37,42,44-49H,8-16H2,1-7H3/t18-,19-,20+,21+,22-,23-,24-,25+,26-,27+,28-,29-,30+,31-,32-,33+,34-,35-,36+,37+,38+,39+,40+,41-/m1/s1
SMILES:	C[C@@H]1[C@H]([C@@H](C[C@@H](O1)O[C@H]2CC[C@]3([C@H](C2)CC[C@]45[C@@H]3[C@@H]([C@H]([C@]6([C@]4(O5)CC[C@@H]6C(=O)C)C)O)O)C)OC)O[C@H]7[C@@H]([C@@H]([C@@H]([C@H](O7)C)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118724169
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

*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	=	165	n.a.	PMID[25215856]
NPT2	Others	Unspecified	IC50	=	150	nM	PMID[25215856]
NPT2	Others	Unspecified	IC50	=	24800	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 NPC477492 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	4421
0.2-0.3	9732
0.3-0.4	12813
0.4-0.5	6611
0.5-0.6	4347
0.6-0.7	2405
0.7-0.8	1508
0.8-0.85	161
0.85-0.9	80
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9619	High Similarity	NPC477489
0.9223	High Similarity	NPC34562
0.9126	High Similarity	NPC310031
0.9126	High Similarity	NPC80191
0.9057	High Similarity	NPC202898
0.9057	High Similarity	NPC475319
0.9057	High Similarity	NPC92890
0.9048	High Similarity	NPC215408
0.8981	High Similarity	NPC469824
0.8972	High Similarity	NPC233433
0.8972	High Similarity	NPC273002
0.8972	High Similarity	NPC94086
0.8972	High Similarity	NPC473817
0.8972	High Similarity	NPC92297
0.8972	High Similarity	NPC220836
0.8952	High Similarity	NPC470167
0.8932	High Similarity	NPC20028
0.8857	High Similarity	NPC107385
0.8846	High Similarity	NPC477172
0.8796	High Similarity	NPC228190
0.8796	High Similarity	NPC236753
0.875	High Similarity	NPC41843
0.8704	High Similarity	NPC469826
0.8655	High Similarity	NPC477493
0.8636	High Similarity	NPC473062
0.8624	High Similarity	NPC208333
0.8624	High Similarity	NPC227879
0.8611	High Similarity	NPC203974
0.8584	High Similarity	NPC179429
0.8532	High Similarity	NPC472079
0.8519	High Similarity	NPC158367
0.8519	High Similarity	NPC119628
0.8519	High Similarity	NPC158051
0.8505	High Similarity	NPC473406
0.8505	High Similarity	NPC471253
0.8487	Intermediate Similarity	NPC114306
0.8487	Intermediate Similarity	NPC477490
0.8482	Intermediate Similarity	NPC97002
0.8455	Intermediate Similarity	NPC87393
0.8455	Intermediate Similarity	NPC469825
0.844	Intermediate Similarity	NPC138219
0.844	Intermediate Similarity	NPC475234
0.844	Intermediate Similarity	NPC126753
0.844	Intermediate Similarity	NPC475630
0.844	Intermediate Similarity	NPC40716
0.8426	Intermediate Similarity	NPC469827
0.8426	Intermediate Similarity	NPC267637
0.8411	Intermediate Similarity	NPC471254
0.8411	Intermediate Similarity	NPC470172
0.8407	Intermediate Similarity	NPC79193
0.8381	Intermediate Similarity	NPC477223
0.8381	Intermediate Similarity	NPC477222
0.8381	Intermediate Similarity	NPC472273
0.8381	Intermediate Similarity	NPC470591
0.8378	Intermediate Similarity	NPC66513
0.8378	Intermediate Similarity	NPC470622
0.8365	Intermediate Similarity	NPC477494
0.8365	Intermediate Similarity	NPC92196
0.8364	Intermediate Similarity	NPC231566
0.8364	Intermediate Similarity	NPC262567
0.8364	Intermediate Similarity	NPC473688
0.8364	Intermediate Similarity	NPC471626
0.835	Intermediate Similarity	NPC137004
0.835	Intermediate Similarity	NPC172838
0.8349	Intermediate Similarity	NPC184805
0.8349	Intermediate Similarity	NPC273189
0.8333	Intermediate Similarity	NPC472718
0.8318	Intermediate Similarity	NPC476839
0.8318	Intermediate Similarity	NPC476838
0.8318	Intermediate Similarity	NPC475574
0.8286	Intermediate Similarity	NPC121453
0.8286	Intermediate Similarity	NPC304011
0.8286	Intermediate Similarity	NPC296936
0.8286	Intermediate Similarity	NPC139271
0.8273	Intermediate Similarity	NPC471430
0.8269	Intermediate Similarity	NPC309866
0.8252	Intermediate Similarity	NPC204881
0.8252	Intermediate Similarity	NPC473830
0.8252	Intermediate Similarity	NPC293609
0.8241	Intermediate Similarity	NPC80640
0.823	Intermediate Similarity	NPC472719
0.823	Intermediate Similarity	NPC157571
0.823	Intermediate Similarity	NPC207845
0.8214	Intermediate Similarity	NPC471431
0.8208	Intermediate Similarity	NPC471241
0.8208	Intermediate Similarity	NPC210157
0.8205	Intermediate Similarity	NPC108072
0.8198	Intermediate Similarity	NPC207693
0.819	Intermediate Similarity	NPC215570
0.819	Intermediate Similarity	NPC94582
0.819	Intermediate Similarity	NPC57964
0.8173	Intermediate Similarity	NPC277774
0.8173	Intermediate Similarity	NPC473726
0.8165	Intermediate Similarity	NPC476837
0.8165	Intermediate Similarity	NPC139181
0.8165	Intermediate Similarity	NPC97260
0.8155	Intermediate Similarity	NPC279329
0.8155	Intermediate Similarity	NPC65550
0.8148	Intermediate Similarity	NPC472081
0.8148	Intermediate Similarity	NPC108227
0.8148	Intermediate Similarity	NPC178853
0.8148	Intermediate Similarity	NPC476512
0.8142	Intermediate Similarity	NPC274833
0.8131	Intermediate Similarity	NPC473518
0.813	Intermediate Similarity	NPC473519
0.813	Intermediate Similarity	NPC473805
0.8125	Intermediate Similarity	NPC22709
0.8113	Intermediate Similarity	NPC142264
0.8113	Intermediate Similarity	NPC476510
0.8113	Intermediate Similarity	NPC473601
0.8113	Intermediate Similarity	NPC195297
0.8095	Intermediate Similarity	NPC253268
0.8095	Intermediate Similarity	NPC477495
0.8095	Intermediate Similarity	NPC3538
0.8095	Intermediate Similarity	NPC252253
0.8095	Intermediate Similarity	NPC24960
0.8095	Intermediate Similarity	NPC475436
0.8095	Intermediate Similarity	NPC113500
0.8095	Intermediate Similarity	NPC174024
0.8095	Intermediate Similarity	NPC222731
0.8095	Intermediate Similarity	NPC291203
0.8095	Intermediate Similarity	NPC291547
0.8095	Intermediate Similarity	NPC473774
0.8095	Intermediate Similarity	NPC473851
0.8095	Intermediate Similarity	NPC217205
0.8095	Intermediate Similarity	NPC179859
0.8095	Intermediate Similarity	NPC305418
0.8095	Intermediate Similarity	NPC312678
0.8095	Intermediate Similarity	NPC477224
0.8095	Intermediate Similarity	NPC131693
0.8095	Intermediate Similarity	NPC45959
0.8095	Intermediate Similarity	NPC294686
0.8087	Intermediate Similarity	NPC477465
0.8077	Intermediate Similarity	NPC36372
0.8073	Intermediate Similarity	NPC470029
0.8073	Intermediate Similarity	NPC114700
0.8073	Intermediate Similarity	NPC310138
0.8073	Intermediate Similarity	NPC134967
0.8065	Intermediate Similarity	NPC102015
0.8058	Intermediate Similarity	NPC131466
0.8058	Intermediate Similarity	NPC473472
0.8056	Intermediate Similarity	NPC80417
0.8037	Intermediate Similarity	NPC470861
0.8037	Intermediate Similarity	NPC115165
0.8037	Intermediate Similarity	NPC83137
0.8037	Intermediate Similarity	NPC51520
0.8037	Intermediate Similarity	NPC303069
0.8037	Intermediate Similarity	NPC470862
0.8037	Intermediate Similarity	NPC470028
0.8037	Intermediate Similarity	NPC233649
0.8037	Intermediate Similarity	NPC232611
0.8037	Intermediate Similarity	NPC476112
0.8037	Intermediate Similarity	NPC274200
0.8037	Intermediate Similarity	NPC307534
0.8019	Intermediate Similarity	NPC107188
0.8019	Intermediate Similarity	NPC107962
0.8019	Intermediate Similarity	NPC211354
0.8019	Intermediate Similarity	NPC6295
0.8019	Intermediate Similarity	NPC19400
0.8019	Intermediate Similarity	NPC206003
0.8019	Intermediate Similarity	NPC473610
0.8019	Intermediate Similarity	NPC475351
0.8019	Intermediate Similarity	NPC474399
0.8019	Intermediate Similarity	NPC473727
0.8018	Intermediate Similarity	NPC166079
0.8018	Intermediate Similarity	NPC306776
0.8	Intermediate Similarity	NPC234352
0.8	Intermediate Similarity	NPC48339
0.8	Intermediate Similarity	NPC325828
0.8	Intermediate Similarity	NPC250393
0.8	Intermediate Similarity	NPC249204
0.8	Intermediate Similarity	NPC297348
0.8	Intermediate Similarity	NPC167644
0.8	Intermediate Similarity	NPC144790
0.8	Intermediate Similarity	NPC177834
0.8	Intermediate Similarity	NPC88962
0.8	Intermediate Similarity	NPC141769
0.8	Intermediate Similarity	NPC311246
0.8	Intermediate Similarity	NPC161035
0.8	Intermediate Similarity	NPC149400
0.8	Intermediate Similarity	NPC477547
0.8	Intermediate Similarity	NPC477451
0.7982	Intermediate Similarity	NPC240734
0.7982	Intermediate Similarity	NPC275668
0.7982	Intermediate Similarity	NPC204392
0.7982	Intermediate Similarity	NPC1876
0.7982	Intermediate Similarity	NPC91838
0.7981	Intermediate Similarity	NPC223143
0.7965	Intermediate Similarity	NPC8431
0.7963	Intermediate Similarity	NPC291548
0.7963	Intermediate Similarity	NPC473638
0.7961	Intermediate Similarity	NPC281004
0.7949	Intermediate Similarity	NPC156651
0.7944	Intermediate Similarity	NPC470863
0.7944	Intermediate Similarity	NPC232037
0.7944	Intermediate Similarity	NPC128572
0.7944	Intermediate Similarity	NPC84111
0.7944	Intermediate Similarity	NPC475625
0.7944	Intermediate Similarity	NPC287483
0.7944	Intermediate Similarity	NPC116756

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 NPC477492 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	643
0.1-0.2	4257
0.2-0.3	2912
0.3-0.4	708
0.4-0.5	345
0.5-0.6	210
0.6-0.7	61
0.7-0.8	13
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
0.8952	High Similarity	NPD8170	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8171	Discontinued
0.7845	Intermediate Similarity	NPD8133	Approved
0.735	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD7507	Approved
0.7143	Intermediate Similarity	NPD8328	Phase 3
0.7132	Intermediate Similarity	NPD7319	Approved
0.712	Intermediate Similarity	NPD8296	Approved
0.712	Intermediate Similarity	NPD8380	Approved
0.712	Intermediate Similarity	NPD8335	Approved
0.712	Intermediate Similarity	NPD8379	Approved
0.712	Intermediate Similarity	NPD8378	Approved
0.7043	Intermediate Similarity	NPD1700	Approved
0.704	Intermediate Similarity	NPD8377	Approved
0.704	Intermediate Similarity	NPD8294	Approved
0.7034	Intermediate Similarity	NPD6412	Phase 2
0.696	Remote Similarity	NPD7516	Approved
0.6923	Remote Similarity	NPD7736	Approved
0.688	Remote Similarity	NPD7328	Approved
0.688	Remote Similarity	NPD7327	Approved
0.6857	Remote Similarity	NPD6928	Phase 2
0.685	Remote Similarity	NPD8033	Approved
0.6833	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6370	Approved
0.672	Remote Similarity	NPD6940	Discontinued
0.6718	Remote Similarity	NPD8293	Discontinued
0.6699	Remote Similarity	NPD3703	Phase 2
0.6667	Remote Similarity	NPD6118	Approved
0.6667	Remote Similarity	NPD6114	Approved
0.6667	Remote Similarity	NPD6115	Approved
0.6667	Remote Similarity	NPD6697	Approved
0.6641	Remote Similarity	NPD6059	Approved
0.6641	Remote Similarity	NPD6054	Approved
0.6571	Remote Similarity	NPD6116	Phase 1
0.6514	Remote Similarity	NPD3669	Approved
0.6514	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD1780	Approved
0.6481	Remote Similarity	NPD1779	Approved
0.648	Remote Similarity	NPD8297	Approved
0.648	Remote Similarity	NPD6882	Approved
0.6476	Remote Similarity	NPD6117	Approved
0.6462	Remote Similarity	NPD6016	Approved
0.6462	Remote Similarity	NPD6015	Approved
0.6439	Remote Similarity	NPD7492	Approved
0.6412	Remote Similarity	NPD5988	Approved
0.6408	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6009	Approved
0.6391	Remote Similarity	NPD6616	Approved
0.6385	Remote Similarity	NPD6319	Approved
0.6381	Remote Similarity	NPD3702	Approved
0.6371	Remote Similarity	NPD6373	Approved
0.6371	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD6372	Approved
0.6348	Remote Similarity	NPD8035	Phase 2
0.6348	Remote Similarity	NPD8034	Phase 2
0.6343	Remote Similarity	NPD7078	Approved
0.6336	Remote Similarity	NPD8517	Approved
0.6336	Remote Similarity	NPD6921	Approved
0.6336	Remote Similarity	NPD8515	Approved
0.6336	Remote Similarity	NPD8516	Approved
0.6336	Remote Similarity	NPD8513	Phase 3
0.6336	Remote Similarity	NPD7503	Approved
0.632	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4244	Approved
0.6311	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4245	Approved
0.6311	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD4632	Approved
0.6286	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.627	Remote Similarity	NPD6649	Approved
0.627	Remote Similarity	NPD6650	Approved
0.626	Remote Similarity	NPD6008	Approved
0.626	Remote Similarity	NPD5739	Approved
0.626	Remote Similarity	NPD6402	Approved
0.626	Remote Similarity	NPD6675	Approved
0.626	Remote Similarity	NPD7128	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)
0.6186	Remote Similarity	NPD7991	Discontinued
0.6176	Remote Similarity	NPD6033	Approved
0.616	Remote Similarity	NPD7320	Approved
0.616	Remote Similarity	NPD6881	Approved
0.616	Remote Similarity	NPD6899	Approved
0.616	Remote Similarity	NPD6686	Approved
0.6154	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD8083	Approved
0.6148	Remote Similarity	NPD8139	Approved
0.6148	Remote Similarity	NPD8082	Approved
0.6148	Remote Similarity	NPD8085	Approved
0.6148	Remote Similarity	NPD8138	Approved
0.6148	Remote Similarity	NPD8086	Approved
0.6148	Remote Similarity	NPD8084	Approved
0.6142	Remote Similarity	NPD8130	Phase 1
0.6132	Remote Similarity	NPD1811	Approved
0.6132	Remote Similarity	NPD1810	Approved
0.6129	Remote Similarity	NPD8393	Approved
0.6119	Remote Similarity	NPD6067	Discontinued
0.6119	Remote Similarity	NPD7604	Phase 2
0.6117	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5360	Phase 3
0.6098	Remote Similarity	NPD8275	Approved
0.6098	Remote Similarity	NPD8276	Approved
0.6095	Remote Similarity	NPD5777	Approved
0.6083	Remote Similarity	NPD4755	Approved
0.608	Remote Similarity	NPD5697	Approved
0.608	Remote Similarity	NPD5701	Approved
0.608	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD4634	Approved
0.6063	Remote Similarity	NPD6883	Approved
0.6063	Remote Similarity	NPD7290	Approved
0.6063	Remote Similarity	NPD7102	Approved
0.6048	Remote Similarity	NPD8081	Approved
0.6031	Remote Similarity	NPD7115	Discovery
0.6016	Remote Similarity	NPD6869	Approved
0.6016	Remote Similarity	NPD6847	Approved
0.6016	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD4789	Approved
0.5984	Remote Similarity	NPD5285	Approved
0.5984	Remote Similarity	NPD5286	Approved
0.5984	Remote Similarity	NPD6014	Approved
0.5984	Remote Similarity	NPD6012	Approved
0.5984	Remote Similarity	NPD4700	Approved
0.5984	Remote Similarity	NPD6013	Approved
0.5984	Remote Similarity	NPD4696	Approved
0.597	Remote Similarity	NPD5983	Phase 2
0.5965	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD6336	Discontinued
0.5906	Remote Similarity	NPD6011	Approved
0.5891	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD5211	Phase 2
0.5887	Remote Similarity	NPD5225	Approved
0.5887	Remote Similarity	NPD5226	Approved
0.5887	Remote Similarity	NPD5224	Approved
0.5887	Remote Similarity	NPD4633	Approved
0.5873	Remote Similarity	NPD4767	Approved
0.5873	Remote Similarity	NPD4768	Approved
0.5856	Remote Similarity	NPD7329	Approved
0.5849	Remote Similarity	NPD2254	Approved
0.5849	Remote Similarity	NPD2687	Approved
0.5849	Remote Similarity	NPD2686	Approved
0.5845	Remote Similarity	NPD8450	Suspended
0.584	Remote Similarity	NPD5175	Approved
0.584	Remote Similarity	NPD5174	Approved
0.5825	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.582	Remote Similarity	NPD7902	Approved
0.5806	Remote Similarity	NPD5223	Approved
0.5794	Remote Similarity	NPD4758	Discontinued
0.5794	Remote Similarity	NPD5141	Approved
0.5794	Remote Similarity	NPD6081	Approved
0.5789	Remote Similarity	NPD4788	Approved
0.5781	Remote Similarity	NPD4729	Approved
0.5781	Remote Similarity	NPD4730	Approved
0.5781	Remote Similarity	NPD8174	Phase 2
0.5775	Remote Similarity	NPD8449	Approved
0.5772	Remote Similarity	NPD7638	Approved
0.5769	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD4802	Phase 2
0.5766	Remote Similarity	NPD5364	Discontinued
0.5766	Remote Similarity	NPD4238	Approved
0.5766	Remote Similarity	NPD3671	Phase 1
0.5763	Remote Similarity	NPD5328	Approved
0.575	Remote Similarity	NPD4202	Approved
0.575	Remote Similarity	NPD6399	Phase 3
0.5728	Remote Similarity	NPD371	Approved
0.5726	Remote Similarity	NPD7639	Approved
0.5726	Remote Similarity	NPD8418	Phase 2
0.5726	Remote Similarity	NPD7640	Approved
0.5714	Remote Similarity	NPD6274	Approved
0.5714	Remote Similarity	NPD4754	Approved
0.5704	Remote Similarity	NPD7100	Approved
0.5704	Remote Similarity	NPD7101	Approved
0.5703	Remote Similarity	NPD8140	Approved
0.5703	Remote Similarity	NPD8307	Discontinued
0.5702	Remote Similarity	NPD7748	Approved
0.5701	Remote Similarity	NPD4787	Phase 1
0.5695	Remote Similarity	NPD7625	Phase 1
0.5692	Remote Similarity	NPD5247	Approved
0.5692	Remote Similarity	NPD5248	Approved
0.5692	Remote Similarity	NPD5250	Approved
0.5692	Remote Similarity	NPD5249	Phase 3
0.5692	Remote Similarity	NPD5251	Approved
0.5691	Remote Similarity	NPD6084	Phase 2
0.5691	Remote Similarity	NPD6083	Phase 2
0.5667	Remote Similarity	NPD6079	Approved
0.5659	Remote Similarity	NPD5128	Approved
0.5635	Remote Similarity	NPD8300	Approved
0.5635	Remote Similarity	NPD7632	Discontinued
0.5635	Remote Similarity	NPD8301	Approved
0.563	Remote Similarity	NPD6335	Approved
0.5625	Remote Similarity	NPD6920	Discontinued
0.562	Remote Similarity	NPD6908	Approved
0.562	Remote Similarity	NPD6909	Approved
0.5619	Remote Similarity	NPD4224	Phase 2
0.5615	Remote Similarity	NPD8305	Approved
0.5615	Remote Similarity	NPD8306	Approved
0.561	Remote Similarity	NPD4697	Phase 3

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