NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	646.41
Volume:	656.532
LogP:	5.442
LogD:	3.954
LogS:	-4.231
# Rotatable Bonds:	5
TPSA:	123.91
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.294
Synthetic Accessibility Score:	7.336
Fsp3:	0.973
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:	-5.29
MDCK Permeability:	1.6788404536782764e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.441

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	91.21786499023438%
Volume Distribution (VD):	1.015
Pgp-substrate:	6.5655412673950195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.825
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.674
CYP2C9-inhibitor:	0.103
CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.672
CYP3A4-substrate:	0.362

ADMET: Excretion

Clearance (CL):	1.75
Half-life (T1/2):	0.374

ADMET: Toxicity

hERG Blockers:	0.815
Human Hepatotoxicity (H-HT):	0.303
Drug-inuced Liver Injury (DILI):	0.366
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.504
Maximum Recommended Daily Dose:	0.879
Skin Sensitization:	0.921
Carcinogencity:	0.09
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC476512

Natural Product ID:	NPC476512
*Common Name:**	2-[(1R,3S,4S,7R,9S,12R,14S,17R,18R,19R,21R,22S)-3,8,8,17,19-pentamethyl-9-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-23,24-dioxaheptacyclo[19.2.1.01,18.03,17.04,14.07,12.012,14]tetracosan-22-yl]propan-2-yl acetate
IUPAC Name:	2-[(1R,3S,4S,7R,9S,12R,14S,17R,18R,19R,21R,22S)-3,8,8,17,19-pentamethyl-9-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-23,24-dioxaheptacyclo[19.2.1.01,18.03,17.04,14.07,12.012,14]tetracosan-22-yl]propan-2-yl acetate
Synonyms:
Standard InCHIKey:	BSKNHARRKCTTBW-LLTFDRQESA-N
Standard InCHI:	InChI=1S/C37H58O9/c1-19-15-22-29(32(5,6)44-20(2)38)46-37(45-22)17-34(8)24-10-9-23-31(3,4)25(43-30-27(41)26(40)21(39)16-42-30)11-12-35(23)18-36(24,35)14-13-33(34,7)28(19)37/h19,21-30,39-41H,9-18H2,1-8H3/t19-,21-,22-,23+,24+,25+,26+,27-,28-,29+,30+,33-,34+,35-,36+,37-/m1/s1
SMILES:	C[C@@H]1C[C@@H]2[C@H](O[C@]3([C@H]1[C@]4(CC[C@@]56C[C@@]57CC[C@@H](C([C@@H]7CC[C@H]6[C@@]4(C3)C)(C)C)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)C)O2)C(C)(C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44559105
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins [CHEMONTID:0001687] Cucurbitacin glycosides

*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
NPO39	Actaea asiatica	Species	Ranunculaceae	Eukaryota	roots, rhizomes	n.a.	n.a.	PMID[17067171]
NPO39	Actaea asiatica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	9830	nM	PMID[17067171]

☑ 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 NPC476512 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	563
0.1-0.2	4783
0.2-0.3	13670
0.3-0.4	10228
0.4-0.5	5857
0.5-0.6	3873
0.6-0.7	2179
0.7-0.8	1184
0.8-0.85	150
0.85-0.9	115
0.9-0.95	73
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC108227
1.0	High Similarity	NPC472081
0.9894	High Similarity	NPC470029
0.9894	High Similarity	NPC310138
0.9894	High Similarity	NPC134967
0.9894	High Similarity	NPC114700
0.9789	High Similarity	NPC476837
0.9789	High Similarity	NPC97260
0.9789	High Similarity	NPC139181
0.9579	High Similarity	NPC475574
0.9579	High Similarity	NPC476839
0.9579	High Similarity	NPC476838
0.957	High Similarity	NPC142264
0.957	High Similarity	NPC237071
0.957	High Similarity	NPC203434
0.957	High Similarity	NPC238796
0.957	High Similarity	NPC476510
0.9474	High Similarity	NPC470030
0.9468	High Similarity	NPC233649
0.9468	High Similarity	NPC470028
0.9362	High Similarity	NPC156377
0.9362	High Similarity	NPC296936
0.9355	High Similarity	NPC175
0.9355	High Similarity	NPC151214
0.9355	High Similarity	NPC191915
0.9355	High Similarity	NPC252253
0.9355	High Similarity	NPC45959
0.9263	High Similarity	NPC475207
0.9263	High Similarity	NPC470591
0.9255	High Similarity	NPC94582
0.9255	High Similarity	NPC473065
0.9255	High Similarity	NPC473064
0.9255	High Similarity	NPC473067
0.9255	High Similarity	NPC57964
0.9247	High Similarity	NPC149400
0.9247	High Similarity	NPC144790
0.9247	High Similarity	NPC473726
0.9247	High Similarity	NPC88962
0.9158	High Similarity	NPC139271
0.9158	High Similarity	NPC304011
0.9158	High Similarity	NPC252056
0.9149	High Similarity	NPC473774
0.9149	High Similarity	NPC131693
0.9149	High Similarity	NPC174024
0.9149	High Similarity	NPC253268
0.9149	High Similarity	NPC475436
0.9149	High Similarity	NPC312678
0.9149	High Similarity	NPC24960
0.9149	High Similarity	NPC473851
0.9149	High Similarity	NPC179859
0.9149	High Similarity	NPC291547
0.914	High Similarity	NPC307167
0.914	High Similarity	NPC210759
0.914	High Similarity	NPC229801
0.9062	High Similarity	NPC210157
0.9062	High Similarity	NPC477223
0.9062	High Similarity	NPC477222
0.9053	High Similarity	NPC474399
0.9043	High Similarity	NPC250393
0.9043	High Similarity	NPC249204
0.9043	High Similarity	NPC297348
0.9043	High Similarity	NPC234352
0.9043	High Similarity	NPC477451
0.9043	High Similarity	NPC325828
0.9043	High Similarity	NPC477547
0.9043	High Similarity	NPC177834
0.9043	High Similarity	NPC48339
0.9043	High Similarity	NPC141769
0.9043	High Similarity	NPC311246
0.9043	High Similarity	NPC167644
0.9032	High Similarity	NPC65550
0.9032	High Similarity	NPC473542
0.8958	High Similarity	NPC121453
0.8947	High Similarity	NPC291203
0.8947	High Similarity	NPC222731
0.8947	High Similarity	NPC113500
0.8947	High Similarity	NPC471464
0.8947	High Similarity	NPC294686
0.8947	High Similarity	NPC30687
0.8947	High Similarity	NPC477224
0.8947	High Similarity	NPC217205
0.8947	High Similarity	NPC264101
0.8947	High Similarity	NPC305418
0.8947	High Similarity	NPC309866
0.8947	High Similarity	NPC3538
0.8936	High Similarity	NPC473830
0.8936	High Similarity	NPC473066
0.8936	High Similarity	NPC204881
0.8936	High Similarity	NPC149966
0.8936	High Similarity	NPC5632
0.8925	High Similarity	NPC82955
0.8925	High Similarity	NPC131466
0.8866	High Similarity	NPC476112
0.8866	High Similarity	NPC274200
0.8866	High Similarity	NPC307534
0.8854	High Similarity	NPC206003
0.8854	High Similarity	NPC19400
0.8854	High Similarity	NPC6295
0.8854	High Similarity	NPC475351
0.8854	High Similarity	NPC473727
0.8854	High Similarity	NPC92196
0.8854	High Similarity	NPC107962
0.8854	High Similarity	NPC107188
0.8854	High Similarity	NPC473610
0.8854	High Similarity	NPC211354
0.8842	High Similarity	NPC137004
0.8842	High Similarity	NPC172838
0.883	High Similarity	NPC279329
0.8824	High Similarity	NPC472079
0.8817	High Similarity	NPC281004
0.8776	High Similarity	NPC292775
0.8776	High Similarity	NPC473518
0.8776	High Similarity	NPC473616
0.8763	High Similarity	NPC470864
0.8763	High Similarity	NPC97700
0.8763	High Similarity	NPC116756
0.8763	High Similarity	NPC470865
0.8763	High Similarity	NPC470866
0.8763	High Similarity	NPC475643
0.8763	High Similarity	NPC128572
0.8763	High Similarity	NPC98018
0.8763	High Similarity	NPC232037
0.8763	High Similarity	NPC284104
0.8763	High Similarity	NPC470863
0.8763	High Similarity	NPC195297
0.8763	High Similarity	NPC30856
0.8763	High Similarity	NPC473601
0.8763	High Similarity	NPC132080
0.8763	High Similarity	NPC84111
0.8763	High Similarity	NPC160426
0.8763	High Similarity	NPC184617
0.8763	High Similarity	NPC287483
0.8763	High Similarity	NPC475625
0.8763	High Similarity	NPC103616
0.8737	High Similarity	NPC59006
0.8737	High Similarity	NPC36372
0.8737	High Similarity	NPC293609
0.8723	High Similarity	NPC20822
0.8723	High Similarity	NPC473472
0.8723	High Similarity	NPC102725
0.8723	High Similarity	NPC228059
0.871	High Similarity	NPC140446
0.871	High Similarity	NPC43912
0.8687	High Similarity	NPC41843
0.8673	High Similarity	NPC115165
0.8673	High Similarity	NPC470862
0.8673	High Similarity	NPC83137
0.8673	High Similarity	NPC232611
0.8673	High Similarity	NPC51520
0.8673	High Similarity	NPC303069
0.8673	High Similarity	NPC470861
0.866	High Similarity	NPC21897
0.8646	High Similarity	NPC256104
0.8646	High Similarity	NPC211845
0.8646	High Similarity	NPC277774
0.8646	High Similarity	NPC182740
0.8646	High Similarity	NPC122083
0.8632	High Similarity	NPC223143
0.86	High Similarity	NPC477172
0.8598	High Similarity	NPC212660
0.8586	High Similarity	NPC209798
0.8586	High Similarity	NPC473638
0.8586	High Similarity	NPC471374
0.8586	High Similarity	NPC471375
0.8586	High Similarity	NPC291548
0.8557	High Similarity	NPC473503
0.8542	High Similarity	NPC473637
0.8542	High Similarity	NPC476668
0.85	High Similarity	NPC471426
0.85	High Similarity	NPC471427
0.85	High Similarity	NPC51579
0.85	High Similarity	NPC471428
0.85	High Similarity	NPC20028
0.8495	Intermediate Similarity	NPC290612
0.8491	Intermediate Similarity	NPC477489
0.8469	Intermediate Similarity	NPC469710
0.8469	Intermediate Similarity	NPC477494
0.8469	Intermediate Similarity	NPC215570
0.8454	Intermediate Similarity	NPC476669
0.8447	Intermediate Similarity	NPC215408
0.8416	Intermediate Similarity	NPC477225
0.8404	Intermediate Similarity	NPC471410
0.8404	Intermediate Similarity	NPC471411
0.8404	Intermediate Similarity	NPC215968
0.8404	Intermediate Similarity	NPC155531
0.8404	Intermediate Similarity	NPC477283
0.8396	Intermediate Similarity	NPC469824
0.8396	Intermediate Similarity	NPC473062
0.8387	Intermediate Similarity	NPC474156
0.8384	Intermediate Similarity	NPC473287
0.8381	Intermediate Similarity	NPC476835
0.8381	Intermediate Similarity	NPC227879
0.8381	Intermediate Similarity	NPC208333
0.8367	Intermediate Similarity	NPC475325
0.8365	Intermediate Similarity	NPC203974
0.835	Intermediate Similarity	NPC469827
0.8349	Intermediate Similarity	NPC179429
0.8333	Intermediate Similarity	NPC79193
0.8333	Intermediate Similarity	NPC310031
0.8333	Intermediate Similarity	NPC80191

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 NPC476512 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	568
0.1-0.2	4448
0.2-0.3	2901
0.3-0.4	650
0.4-0.5	346
0.5-0.6	181
0.6-0.7	40
0.7-0.8	14
0.8-0.85	0
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9043	High Similarity	NPD8171	Discontinued
0.8529	High Similarity	NPD8170	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD8294	Approved
0.7965	Intermediate Similarity	NPD8377	Approved
0.7957	Intermediate Similarity	NPD6928	Phase 2
0.7895	Intermediate Similarity	NPD8380	Approved
0.7895	Intermediate Similarity	NPD8379	Approved
0.7895	Intermediate Similarity	NPD8378	Approved
0.7895	Intermediate Similarity	NPD8296	Approved
0.7895	Intermediate Similarity	NPD8335	Approved
0.7895	Intermediate Similarity	NPD8033	Approved
0.7748	Intermediate Similarity	NPD8133	Approved
0.7632	Intermediate Similarity	NPD7328	Approved
0.7632	Intermediate Similarity	NPD7327	Approved
0.7565	Intermediate Similarity	NPD7516	Approved
0.719	Intermediate Similarity	NPD7507	Approved
0.7143	Intermediate Similarity	NPD7503	Approved
0.708	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7991	Discontinued
0.7016	Intermediate Similarity	NPD7319	Approved
0.7	Intermediate Similarity	NPD3669	Approved
0.7	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7736	Approved
0.6882	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6940	Discontinued
0.6837	Remote Similarity	NPD6697	Approved
0.6837	Remote Similarity	NPD6118	Approved
0.6837	Remote Similarity	NPD6114	Approved
0.6837	Remote Similarity	NPD6115	Approved
0.6771	Remote Similarity	NPD1810	Approved
0.6771	Remote Similarity	NPD1811	Approved
0.6754	Remote Similarity	NPD6412	Phase 2
0.6735	Remote Similarity	NPD6116	Phase 1
0.672	Remote Similarity	NPD8293	Discontinued
0.6633	Remote Similarity	NPD6117	Approved
0.6613	Remote Similarity	NPD8328	Phase 3
0.6532	Remote Similarity	NPD6370	Approved
0.646	Remote Similarity	NPD1700	Approved
0.6458	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD2254	Approved
0.6458	Remote Similarity	NPD2687	Approved
0.6458	Remote Similarity	NPD2686	Approved
0.6429	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7492	Approved
0.6378	Remote Similarity	NPD6616	Approved
0.6371	Remote Similarity	NPD6059	Approved
0.6371	Remote Similarity	NPD6054	Approved
0.6364	Remote Similarity	NPD3702	Approved
0.6336	Remote Similarity	NPD8449	Approved
0.6331	Remote Similarity	NPD7625	Phase 1
0.633	Remote Similarity	NPD8035	Phase 2
0.633	Remote Similarity	NPD8034	Phase 2
0.6328	Remote Similarity	NPD7078	Approved
0.6311	Remote Similarity	NPD1779	Approved
0.6311	Remote Similarity	NPD1780	Approved
0.6293	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4787	Phase 1
0.6288	Remote Similarity	NPD8450	Suspended
0.6271	Remote Similarity	NPD6686	Approved
0.6271	Remote Similarity	NPD8174	Phase 2
0.6198	Remote Similarity	NPD6882	Approved
0.6198	Remote Similarity	NPD8297	Approved
0.619	Remote Similarity	NPD6016	Approved
0.619	Remote Similarity	NPD6015	Approved
0.6142	Remote Similarity	NPD5988	Approved
0.614	Remote Similarity	NPD7638	Approved
0.6129	Remote Similarity	NPD6009	Approved
0.6111	Remote Similarity	NPD6319	Approved
0.6094	Remote Similarity	NPD6067	Discontinued
0.6087	Remote Similarity	NPD7640	Approved
0.6087	Remote Similarity	NPD7639	Approved
0.6075	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD8513	Phase 3
0.6063	Remote Similarity	NPD8517	Approved
0.6063	Remote Similarity	NPD8515	Approved
0.6063	Remote Similarity	NPD8516	Approved
0.6061	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5777	Approved
0.604	Remote Similarity	NPD3703	Phase 2
0.6016	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7320	Approved
0.6	Remote Similarity	NPD371	Approved
0.5983	Remote Similarity	NPD7632	Discontinued
0.5969	Remote Similarity	NPD7604	Phase 2
0.5966	Remote Similarity	NPD6008	Approved
0.5966	Remote Similarity	NPD7128	Approved
0.5966	Remote Similarity	NPD6402	Approved
0.5966	Remote Similarity	NPD6675	Approved
0.5966	Remote Similarity	NPD5739	Approved
0.596	Remote Similarity	NPD4245	Approved
0.596	Remote Similarity	NPD4244	Approved
0.595	Remote Similarity	NPD6373	Approved
0.595	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.595	Remote Similarity	NPD6372	Approved
0.5917	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6033	Approved
0.5905	Remote Similarity	NPD7525	Registered
0.5868	Remote Similarity	NPD6899	Approved
0.5868	Remote Similarity	NPD6881	Approved
0.5859	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD3698	Phase 2
0.5854	Remote Similarity	NPD6649	Approved
0.5854	Remote Similarity	NPD8130	Phase 1
0.5854	Remote Similarity	NPD6650	Approved
0.5812	Remote Similarity	NPD8418	Phase 2
0.5785	Remote Similarity	NPD5701	Approved
0.5785	Remote Similarity	NPD5697	Approved
0.5772	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD7102	Approved
0.5772	Remote Similarity	NPD7290	Approved
0.5772	Remote Similarity	NPD6883	Approved
0.5758	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD5360	Phase 3
0.5748	Remote Similarity	NPD7115	Discovery
0.5743	Remote Similarity	NPD6081	Approved
0.5739	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD6617	Approved
0.5726	Remote Similarity	NPD6869	Approved
0.5726	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD6847	Approved
0.5714	Remote Similarity	NPD8086	Approved
0.5714	Remote Similarity	NPD8082	Approved
0.5714	Remote Similarity	NPD8085	Approved
0.5714	Remote Similarity	NPD8138	Approved
0.5714	Remote Similarity	NPD8084	Approved
0.5714	Remote Similarity	NPD8139	Approved
0.5714	Remote Similarity	NPD8083	Approved
0.5692	Remote Similarity	NPD5983	Phase 2
0.5691	Remote Similarity	NPD6012	Approved
0.5691	Remote Similarity	NPD6013	Approved
0.5691	Remote Similarity	NPD6014	Approved
0.5669	Remote Similarity	NPD7754	Approved
0.5669	Remote Similarity	NPD7755	Approved
0.5667	Remote Similarity	NPD8276	Approved
0.5667	Remote Similarity	NPD7986	Approved
0.5667	Remote Similarity	NPD7912	Approved
0.5667	Remote Similarity	NPD7987	Approved
0.5667	Remote Similarity	NPD8275	Approved
0.5667	Remote Similarity	NPD7911	Approved
0.5652	Remote Similarity	NPD7748	Approved
0.5644	Remote Similarity	NPD4789	Approved
0.5641	Remote Similarity	NPD6083	Phase 2
0.5641	Remote Similarity	NPD6084	Phase 2
0.5641	Remote Similarity	NPD7902	Approved
0.5639	Remote Similarity	NPD6336	Discontinued
0.562	Remote Similarity	NPD8081	Approved
0.561	Remote Similarity	NPD6011	Approved
0.56	Remote Similarity	NPD6401	Clinical (unspecified phase)

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