NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	912.47
Volume:	886.035
LogP:	2.336
LogD:	2.344
LogS:	-3.83
# Rotatable Bonds:	13
TPSA:	251.12
# H-Bond Aceptor:	18
# H-Bond Donor:	6
# Rings:	8
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.07
Synthetic Accessibility Score:	7.244
Fsp3:	0.913
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:	-5.906
MDCK Permeability:	0.00022295734379440546
Pgp-inhibitor:	0.948
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.197
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.548

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055
Plasma Protein Binding (PPB):	46.8487548828125%
Volume Distribution (VD):	0.47
Pgp-substrate:	13.695615768432617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.99
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.672
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.177
CYP3A4-substrate:	0.656

ADMET: Excretion

Clearance (CL):	2.017
Half-life (T1/2):	0.641

ADMET: Toxicity

hERG Blockers:	0.697
Human Hepatotoxicity (H-HT):	0.253
Drug-inuced Liver Injury (DILI):	0.14
AMES Toxicity:	0.12
Rat Oral Acute Toxicity:	0.242
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.285
Carcinogencity:	0.149
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: NPC477493

Natural Product ID:	NPC477493
*Common Name:**	[(1S,3R,6S,7S,8S,9S,10S,11S,14S,16S)-6-acetyl-8-hydroxy-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-9-yl] (E)-2-methylbut-2-enoate
IUPAC Name:	[(1S,3R,6S,7S,8S,9S,10S,11S,14S,16S)-6-acetyl-8-hydroxy-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-9-yl] (E)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	BCQPDWXLZYJFGT-SNTJMDAJSA-N
Standard InCHI:	InChI=1S/C46H72O18/c1-10-20(2)40(54)61-37-38-43(6)14-12-25(17-24(43)11-15-45(38)46(64-45)16-13-26(21(3)48)44(46,7)39(37)53)59-29-18-27(55-8)34(22(4)57-29)62-42-33(52)36(56-9)35(23(5)58-42)63-41-32(51)31(50)30(49)28(19-47)60-41/h10,22-39,41-42,47,49-53H,11-19H2,1-9H3/b20-10+/t22-,23-,24+,25+,26-,27-,28-,29+,30-,31+,32-,33-,34-,35-,36+,37+,38-,39-,41+,42+,43+,44+,45+,46-/m1/s1
SMILES:	C/C=C(\C)/C(=O)O[C@H]1[C@@H]2[C@]3(CC[C@@H](C[C@@H]3CC[C@@]24[C@@]5(O4)CC[C@@H]([C@]5([C@@H]1O)C)C(=O)C)O[C@H]6C[C@H]([C@@H]([C@H](O6)C)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)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118724170
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	=	133	n.a.	PMID[25215856]
NPT2	Others	Unspecified	IC50	=	180	nM	PMID[25215856]
NPT2	Others	Unspecified	IC50	=	23900	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 NPC477493 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	382
0.1-0.2	2555
0.2-0.3	6459
0.3-0.4	11005
0.4-0.5	9783
0.5-0.6	6384
0.6-0.7	3740
0.7-0.8	2073
0.8-0.85	269
0.85-0.9	44
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9832	High Similarity	NPC114306
0.9832	High Similarity	NPC477490
0.8846	High Similarity	NPC290746
0.8846	High Similarity	NPC79250
0.875	High Similarity	NPC477709
0.875	High Similarity	NPC476221
0.8692	High Similarity	NPC59288
0.8672	High Similarity	NPC93416
0.8655	High Similarity	NPC477492
0.8655	High Similarity	NPC477489
0.8651	High Similarity	NPC240070
0.8651	High Similarity	NPC329784
0.8615	High Similarity	NPC194716
0.8594	High Similarity	NPC16569
0.8594	High Similarity	NPC159338
0.8594	High Similarity	NPC253456
0.855	High Similarity	NPC329675
0.8538	High Similarity	NPC329636
0.8527	High Similarity	NPC19124
0.8527	High Similarity	NPC471855
0.8527	High Similarity	NPC42670
0.8516	High Similarity	NPC276838
0.8516	High Similarity	NPC125077
0.8516	High Similarity	NPC329986
0.8516	High Similarity	NPC232785
0.8516	High Similarity	NPC140092
0.8516	High Similarity	NPC188234
0.8516	High Similarity	NPC91
0.8462	Intermediate Similarity	NPC469749
0.8462	Intermediate Similarity	NPC116075
0.8462	Intermediate Similarity	NPC225385
0.8462	Intermediate Similarity	NPC142756
0.8462	Intermediate Similarity	NPC32793
0.8462	Intermediate Similarity	NPC298783
0.8462	Intermediate Similarity	NPC247190
0.8462	Intermediate Similarity	NPC104585
0.8462	Intermediate Similarity	NPC146857
0.8462	Intermediate Similarity	NPC157817
0.8413	Intermediate Similarity	NPC27363
0.8385	Intermediate Similarity	NPC473805
0.8385	Intermediate Similarity	NPC473519
0.8372	Intermediate Similarity	NPC471407
0.8359	Intermediate Similarity	NPC471356
0.8359	Intermediate Similarity	NPC471357
0.8359	Intermediate Similarity	NPC179412
0.8359	Intermediate Similarity	NPC146456
0.8359	Intermediate Similarity	NPC117702
0.8359	Intermediate Similarity	NPC469757
0.8333	Intermediate Similarity	NPC28532
0.8333	Intermediate Similarity	NPC264336
0.8321	Intermediate Similarity	NPC102015
0.8321	Intermediate Similarity	NPC316915
0.832	Intermediate Similarity	NPC108072
0.8308	Intermediate Similarity	NPC173347
0.8293	Intermediate Similarity	NPC472718
0.8281	Intermediate Similarity	NPC250556
0.8281	Intermediate Similarity	NPC469750
0.8271	Intermediate Similarity	NPC127656
0.8268	Intermediate Similarity	NPC308262
0.8268	Intermediate Similarity	NPC208193
0.8268	Intermediate Similarity	NPC117445
0.8254	Intermediate Similarity	NPC173555
0.8254	Intermediate Similarity	NPC120390
0.8254	Intermediate Similarity	NPC475590
0.8254	Intermediate Similarity	NPC475419
0.8254	Intermediate Similarity	NPC474908
0.8254	Intermediate Similarity	NPC314535
0.8244	Intermediate Similarity	NPC231240
0.8231	Intermediate Similarity	NPC469754
0.8231	Intermediate Similarity	NPC471352
0.8231	Intermediate Similarity	NPC10823
0.8231	Intermediate Similarity	NPC284406
0.8231	Intermediate Similarity	NPC469752
0.8231	Intermediate Similarity	NPC469755
0.8231	Intermediate Similarity	NPC471358
0.8231	Intermediate Similarity	NPC6108
0.8231	Intermediate Similarity	NPC471361
0.8231	Intermediate Similarity	NPC471360
0.8231	Intermediate Similarity	NPC70542
0.8231	Intermediate Similarity	NPC89514
0.8231	Intermediate Similarity	NPC251866
0.8231	Intermediate Similarity	NPC469751
0.8231	Intermediate Similarity	NPC471359
0.8231	Intermediate Similarity	NPC219085
0.8231	Intermediate Similarity	NPC86159
0.8231	Intermediate Similarity	NPC476966
0.8231	Intermediate Similarity	NPC17896
0.8231	Intermediate Similarity	NPC197707
0.8231	Intermediate Similarity	NPC180079
0.8231	Intermediate Similarity	NPC469753
0.8231	Intermediate Similarity	NPC9499
0.8217	Intermediate Similarity	NPC470516
0.8197	Intermediate Similarity	NPC207845
0.8197	Intermediate Similarity	NPC472719
0.8195	Intermediate Similarity	NPC171619
0.8189	Intermediate Similarity	NPC74259
0.8189	Intermediate Similarity	NPC474423
0.8175	Intermediate Similarity	NPC475556
0.8175	Intermediate Similarity	NPC474466
0.8175	Intermediate Similarity	NPC470312
0.8175	Intermediate Similarity	NPC475136
0.8175	Intermediate Similarity	NPC135369
0.8175	Intermediate Similarity	NPC475629
0.8175	Intermediate Similarity	NPC281840
0.8175	Intermediate Similarity	NPC72260
0.8154	Intermediate Similarity	NPC220838
0.8154	Intermediate Similarity	NPC45606
0.8154	Intermediate Similarity	NPC311534
0.8134	Intermediate Similarity	NPC62172
0.8134	Intermediate Similarity	NPC141215
0.8134	Intermediate Similarity	NPC289700
0.8134	Intermediate Similarity	NPC190065
0.8134	Intermediate Similarity	NPC471089
0.8115	Intermediate Similarity	NPC469824
0.8115	Intermediate Similarity	NPC274833
0.8106	Intermediate Similarity	NPC476776
0.8106	Intermediate Similarity	NPC478154
0.8102	Intermediate Similarity	NPC5153
0.8102	Intermediate Similarity	NPC48414
0.8095	Intermediate Similarity	NPC30483
0.8095	Intermediate Similarity	NPC470897
0.8095	Intermediate Similarity	NPC469756
0.8095	Intermediate Similarity	NPC55532
0.8095	Intermediate Similarity	NPC292467
0.8095	Intermediate Similarity	NPC236973
0.8095	Intermediate Similarity	NPC329905
0.8095	Intermediate Similarity	NPC32177
0.8095	Intermediate Similarity	NPC473401
0.8092	Intermediate Similarity	NPC280029
0.8092	Intermediate Similarity	NPC470518
0.8092	Intermediate Similarity	NPC1314
0.8092	Intermediate Similarity	NPC252657
0.8092	Intermediate Similarity	NPC273878
0.8092	Intermediate Similarity	NPC244296
0.8092	Intermediate Similarity	NPC252289
0.8092	Intermediate Similarity	NPC82380
0.8092	Intermediate Similarity	NPC9470
0.8092	Intermediate Similarity	NPC115656
0.8092	Intermediate Similarity	NPC472267
0.8092	Intermediate Similarity	NPC88311
0.8092	Intermediate Similarity	NPC477196
0.8092	Intermediate Similarity	NPC269484
0.8092	Intermediate Similarity	NPC107536
0.8092	Intermediate Similarity	NPC97918
0.8092	Intermediate Similarity	NPC11577
0.8092	Intermediate Similarity	NPC231529
0.8092	Intermediate Similarity	NPC141600
0.8092	Intermediate Similarity	NPC305793
0.808	Intermediate Similarity	NPC78836
0.808	Intermediate Similarity	NPC473304
0.8077	Intermediate Similarity	NPC42399
0.8077	Intermediate Similarity	NPC298841
0.8074	Intermediate Similarity	NPC596
0.8074	Intermediate Similarity	NPC295885
0.8074	Intermediate Similarity	NPC140045
0.8062	Intermediate Similarity	NPC473505
0.806	Intermediate Similarity	NPC262813
0.8047	Intermediate Similarity	NPC193893
0.8045	Intermediate Similarity	NPC478151
0.8031	Intermediate Similarity	NPC476150
0.8031	Intermediate Similarity	NPC476127
0.803	Intermediate Similarity	NPC471170
0.803	Intermediate Similarity	NPC476780
0.803	Intermediate Similarity	NPC271610
0.803	Intermediate Similarity	NPC478155
0.803	Intermediate Similarity	NPC476774
0.803	Intermediate Similarity	NPC43589
0.803	Intermediate Similarity	NPC477197
0.803	Intermediate Similarity	NPC25998
0.803	Intermediate Similarity	NPC476775
0.803	Intermediate Similarity	NPC300655
0.803	Intermediate Similarity	NPC222951
0.803	Intermediate Similarity	NPC311178
0.8016	Intermediate Similarity	NPC83287
0.8016	Intermediate Similarity	NPC471548
0.8015	Intermediate Similarity	NPC75616
0.8015	Intermediate Similarity	NPC270109
0.8015	Intermediate Similarity	NPC477193
0.8015	Intermediate Similarity	NPC477191
0.8015	Intermediate Similarity	NPC473620
0.8015	Intermediate Similarity	NPC477194
0.8015	Intermediate Similarity	NPC477192
0.8015	Intermediate Similarity	NPC245094
0.8	Intermediate Similarity	NPC16729
0.8	Intermediate Similarity	NPC229752
0.8	Intermediate Similarity	NPC251998
0.8	Intermediate Similarity	NPC475462
0.8	Intermediate Similarity	NPC473635
0.8	Intermediate Similarity	NPC88945
0.8	Intermediate Similarity	NPC297950
0.8	Intermediate Similarity	NPC471816
0.7986	Intermediate Similarity	NPC471172
0.7985	Intermediate Similarity	NPC248703
0.7985	Intermediate Similarity	NPC476778
0.7985	Intermediate Similarity	NPC476777
0.7983	Intermediate Similarity	NPC34562
0.797	Intermediate Similarity	NPC478150
0.797	Intermediate Similarity	NPC183816
0.797	Intermediate Similarity	NPC475444
0.797	Intermediate Similarity	NPC477195

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 NPC477493 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	391
0.1-0.2	2743
0.2-0.3	3845
0.3-0.4	1367
0.4-0.5	427
0.5-0.6	247
0.6-0.7	104
0.7-0.8	13
0.8-0.85	13
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8281	Intermediate Similarity	NPD7507	Approved
0.8279	Intermediate Similarity	NPD8133	Approved
0.8254	Intermediate Similarity	NPD8296	Approved
0.8254	Intermediate Similarity	NPD8335	Approved
0.8254	Intermediate Similarity	NPD8378	Approved
0.8254	Intermediate Similarity	NPD8380	Approved
0.8254	Intermediate Similarity	NPD8379	Approved
0.8231	Intermediate Similarity	NPD7319	Approved
0.8175	Intermediate Similarity	NPD8377	Approved
0.8175	Intermediate Similarity	NPD8294	Approved
0.8095	Intermediate Similarity	NPD7516	Approved
0.8016	Intermediate Similarity	NPD7328	Approved
0.8016	Intermediate Similarity	NPD7327	Approved
0.7969	Intermediate Similarity	NPD8033	Approved
0.7769	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD8328	Phase 3
0.7612	Intermediate Similarity	NPD7736	Approved
0.7557	Intermediate Similarity	NPD7503	Approved
0.744	Intermediate Similarity	NPD6686	Approved
0.736	Intermediate Similarity	NPD6412	Phase 2
0.7279	Intermediate Similarity	NPD8293	Discontinued
0.7252	Intermediate Similarity	NPD7115	Discovery
0.7244	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6370	Approved
0.7209	Intermediate Similarity	NPD6882	Approved
0.7209	Intermediate Similarity	NPD8297	Approved
0.7165	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD8513	Phase 3
0.7164	Intermediate Similarity	NPD8515	Approved
0.7164	Intermediate Similarity	NPD8517	Approved
0.7164	Intermediate Similarity	NPD8516	Approved
0.7132	Intermediate Similarity	NPD7492	Approved
0.7121	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD6009	Approved
0.7109	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6054	Approved
0.709	Intermediate Similarity	NPD6319	Approved
0.708	Intermediate Similarity	NPD6616	Approved
0.7054	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7078	Approved
0.7023	Intermediate Similarity	NPD4632	Approved
0.7	Intermediate Similarity	NPD6650	Approved
0.7	Intermediate Similarity	NPD6649	Approved
0.6977	Remote Similarity	NPD6373	Approved
0.6977	Remote Similarity	NPD6372	Approved
0.6963	Remote Similarity	NPD6059	Approved
0.6942	Remote Similarity	NPD8171	Discontinued
0.6935	Remote Similarity	NPD7638	Approved
0.6912	Remote Similarity	NPD6015	Approved
0.6912	Remote Similarity	NPD6016	Approved
0.6899	Remote Similarity	NPD6881	Approved
0.6899	Remote Similarity	NPD6899	Approved
0.688	Remote Similarity	NPD7639	Approved
0.688	Remote Similarity	NPD7640	Approved
0.6875	Remote Similarity	NPD7128	Approved
0.6875	Remote Similarity	NPD6008	Approved
0.6875	Remote Similarity	NPD5739	Approved
0.6875	Remote Similarity	NPD6402	Approved
0.6875	Remote Similarity	NPD6675	Approved
0.687	Remote Similarity	NPD8130	Phase 1
0.6861	Remote Similarity	NPD5988	Approved
0.6822	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5697	Approved
0.6812	Remote Similarity	NPD7604	Phase 2
0.6794	Remote Similarity	NPD7102	Approved
0.6794	Remote Similarity	NPD6883	Approved
0.6794	Remote Similarity	NPD7290	Approved
0.6769	Remote Similarity	NPD7320	Approved
0.6742	Remote Similarity	NPD6847	Approved
0.6742	Remote Similarity	NPD6617	Approved
0.6742	Remote Similarity	NPD6869	Approved
0.6718	Remote Similarity	NPD6012	Approved
0.6718	Remote Similarity	NPD6014	Approved
0.6718	Remote Similarity	NPD6013	Approved
0.6692	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD5983	Phase 2
0.6667	Remote Similarity	NPD6921	Approved
0.6645	Remote Similarity	NPD7625	Phase 1
0.6641	Remote Similarity	NPD6011	Approved
0.6617	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6336	Discontinued
0.6541	Remote Similarity	NPD4634	Approved
0.6512	Remote Similarity	NPD5211	Phase 2
0.6503	Remote Similarity	NPD6033	Approved
0.6493	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4696	Approved
0.6484	Remote Similarity	NPD5285	Approved
0.6484	Remote Similarity	NPD5286	Approved
0.6457	Remote Similarity	NPD4755	Approved
0.6457	Remote Similarity	NPD7902	Approved
0.6454	Remote Similarity	NPD6067	Discontinued
0.6452	Remote Similarity	NPD8035	Phase 2
0.6452	Remote Similarity	NPD8034	Phase 2
0.6444	Remote Similarity	NPD6053	Discontinued
0.6434	Remote Similarity	NPD5344	Discontinued
0.6434	Remote Similarity	NPD1700	Approved
0.6423	Remote Similarity	NPD6274	Approved
0.6418	Remote Similarity	NPD6371	Approved
0.6412	Remote Similarity	NPD5141	Approved
0.6403	Remote Similarity	NPD7101	Approved
0.6403	Remote Similarity	NPD7100	Approved
0.6385	Remote Similarity	NPD5225	Approved
0.6385	Remote Similarity	NPD5226	Approved
0.6385	Remote Similarity	NPD7632	Discontinued
0.6385	Remote Similarity	NPD5224	Approved
0.6385	Remote Similarity	NPD4633	Approved
0.6357	Remote Similarity	NPD4700	Approved
0.6349	Remote Similarity	NPD7748	Approved
0.6336	Remote Similarity	NPD5175	Approved
0.6336	Remote Similarity	NPD5174	Approved
0.6331	Remote Similarity	NPD6335	Approved
0.6331	Remote Similarity	NPD7799	Discontinued
0.6328	Remote Similarity	NPD6084	Phase 2
0.6328	Remote Similarity	NPD6083	Phase 2
0.6319	Remote Similarity	NPD8074	Phase 3
0.6308	Remote Similarity	NPD5223	Approved
0.6279	Remote Similarity	NPD4225	Approved
0.6269	Remote Similarity	NPD4730	Approved
0.6269	Remote Similarity	NPD4729	Approved
0.6259	Remote Similarity	NPD6317	Approved
0.6241	Remote Similarity	NPD4767	Approved
0.6241	Remote Similarity	NPD4768	Approved
0.624	Remote Similarity	NPD46	Approved
0.624	Remote Similarity	NPD6698	Approved
0.622	Remote Similarity	NPD7900	Approved
0.622	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD8338	Approved
0.6214	Remote Similarity	NPD6314	Approved
0.6214	Remote Similarity	NPD6313	Approved
0.6197	Remote Similarity	NPD6909	Approved
0.6197	Remote Similarity	NPD6908	Approved
0.6197	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7515	Phase 2
0.619	Remote Similarity	NPD6079	Approved
0.6187	Remote Similarity	NPD6940	Discontinued
0.6176	Remote Similarity	NPD5251	Approved
0.6176	Remote Similarity	NPD5248	Approved
0.6176	Remote Similarity	NPD5250	Approved
0.6176	Remote Similarity	NPD5249	Phase 3
0.6176	Remote Similarity	NPD5247	Approved
0.6172	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.616	Remote Similarity	NPD5328	Approved
0.6154	Remote Similarity	NPD5696	Approved
0.6154	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD7260	Phase 2
0.6148	Remote Similarity	NPD5128	Approved
0.6142	Remote Similarity	NPD6399	Phase 3
0.6142	Remote Similarity	NPD4202	Approved
0.6111	Remote Similarity	NPD7830	Approved
0.6111	Remote Similarity	NPD7829	Approved
0.6107	Remote Similarity	NPD6648	Approved
0.6098	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.609	Remote Similarity	NPD4754	Approved
0.608	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD8336	Approved
0.6054	Remote Similarity	NPD8337	Approved
0.605	Remote Similarity	NPD6697	Approved
0.605	Remote Similarity	NPD6114	Approved
0.605	Remote Similarity	NPD6118	Approved
0.605	Remote Similarity	NPD6115	Approved
0.6047	Remote Similarity	NPD5695	Phase 3
0.6014	Remote Similarity	NPD5216	Approved
0.6014	Remote Similarity	NPD5217	Approved
0.6014	Remote Similarity	NPD5215	Approved
0.6	Remote Similarity	NPD5222	Approved
0.6	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7642	Approved
0.6	Remote Similarity	NPD5221	Approved
0.5973	Remote Similarity	NPD5956	Approved
0.5966	Remote Similarity	NPD6116	Phase 1
0.596	Remote Similarity	NPD8450	Suspended
0.5957	Remote Similarity	NPD6868	Approved
0.5954	Remote Similarity	NPD5173	Approved
0.595	Remote Similarity	NPD6928	Phase 2
0.5942	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD5169	Approved
0.5942	Remote Similarity	NPD5135	Approved
0.5938	Remote Similarity	NPD7236	Approved
0.5938	Remote Similarity	NPD5693	Phase 1
0.5935	Remote Similarity	NPD4788	Approved
0.5935	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD3669	Approved
0.5923	Remote Similarity	NPD5210	Approved
0.5923	Remote Similarity	NPD4629	Approved
0.592	Remote Similarity	NPD7334	Approved
0.592	Remote Similarity	NPD7521	Approved
0.592	Remote Similarity	NPD5330	Approved
0.592	Remote Similarity	NPD6409	Approved
0.592	Remote Similarity	NPD7146	Approved
0.592	Remote Similarity	NPD6684	Approved
0.592	Remote Similarity	NPD3618	Phase 1
0.5906	Remote Similarity	NPD4753	Phase 2
0.5902	Remote Similarity	NPD1780	Approved
0.5902	Remote Similarity	NPD1779	Approved
0.5899	Remote Similarity	NPD5127	Approved
0.5894	Remote Similarity	NPD6845	Suspended
0.5894	Remote Similarity	NPD8449	Approved
0.5882	Remote Similarity	NPD6117	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