NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	348.23
Volume:	367.434
LogP:	2.421
LogD:	2.036
LogS:	-3.639
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.748
Synthetic Accessibility Score:	6.248
Fsp3:	0.857
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.275
MDCK Permeability:	1.9071632777922787e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.027
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.165

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.239
Plasma Protein Binding (PPB):	87.75814056396484%
Volume Distribution (VD):	0.451
Pgp-substrate:	14.285521507263184%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.875
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.679
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.169
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.143
CYP3A4-inhibitor:	0.431
CYP3A4-substrate:	0.139

ADMET: Excretion

Clearance (CL):	2.21
Half-life (T1/2):	0.622

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.653
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.62
Maximum Recommended Daily Dose:	0.057
Skin Sensitization:	0.622
Carcinogencity:	0.051
Eye Corrosion:	0.131
Eye Irritation:	0.259
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC477854

Natural Product ID:	NPC477854
*Common Name:**	(1R,4R,5R,8R,9S,10S,13S,14S)-8-hydroxy-14-methoxy-5,9,14-trimethyltetracyclo[11.2.1.01,10.04,9]hexadec-11-ene-5-carboxylic acid
IUPAC Name:	(1R,4R,5R,8R,9S,10S,13S,14S)-8-hydroxy-14-methoxy-5,9,14-trimethyltetracyclo[11.2.1.01,10.04,9]hexadec-11-ene-5-carboxylic acid
Synonyms:
Standard InCHIKey:	JMCDUBQYQMSCGT-YLKIOQGFSA-N
Standard InCHI:	InChI=1S/C21H32O4/c1-18(17(23)24)9-8-16(22)20(3)14(18)7-10-21-11-13(5-6-15(20)21)19(2,12-21)25-4/h5-6,13-16,22H,7-12H2,1-4H3,(H,23,24)/t13-,14+,15-,16-,18-,19+,20+,21-/m1/s1
SMILES:	C[C@]1(CC[C@H]([C@]2([C@H]1CC[C@@]34[C@@H]2C=C[C@H](C3)[C@@](C4)(C)OC)C)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	46907077
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO33608	Rhizopus arrhizus	Species	Rhizopodaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20481544]

☑ 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

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	10000	nM	PMID[20481544]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	10000	nM	PMID[20481544]

☑ 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 NPC477854 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	185
0.1-0.2	1145
0.2-0.3	4542
0.3-0.4	11796
0.4-0.5	9954
0.5-0.6	5878
0.6-0.7	5721
0.7-0.8	3108
0.8-0.85	319
0.85-0.9	45
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.978	High Similarity	NPC477853
0.9355	High Similarity	NPC173272
0.9247	High Similarity	NPC48330
0.899	High Similarity	NPC231530
0.899	High Similarity	NPC278628
0.8958	High Similarity	NPC114274
0.8889	High Similarity	NPC29705
0.8866	High Similarity	NPC83709
0.8854	High Similarity	NPC108078
0.8854	High Similarity	NPC190554
0.8842	High Similarity	NPC279974
0.8842	High Similarity	NPC469599
0.883	High Similarity	NPC470376
0.883	High Similarity	NPC470375
0.883	High Similarity	NPC477855
0.883	High Similarity	NPC206810
0.8824	High Similarity	NPC197428
0.8812	High Similarity	NPC94529
0.8788	High Similarity	NPC140723
0.871	High Similarity	NPC474704
0.871	High Similarity	NPC475921
0.87	High Similarity	NPC471293
0.87	High Similarity	NPC477812
0.8696	High Similarity	NPC474684
0.8696	High Similarity	NPC142361
0.8687	High Similarity	NPC22388
0.8687	High Similarity	NPC271980
0.8687	High Similarity	NPC193934
0.8687	High Similarity	NPC477054
0.8673	High Similarity	NPC218383
0.8673	High Similarity	NPC15390
0.8654	High Similarity	NPC280782
0.8654	High Similarity	NPC71348
0.8646	High Similarity	NPC470016
0.8646	High Similarity	NPC317586
0.8617	High Similarity	NPC471896
0.8614	High Similarity	NPC196528
0.8602	High Similarity	NPC242864
0.86	High Similarity	NPC222153
0.86	High Similarity	NPC191892
0.8587	High Similarity	NPC73038
0.8587	High Similarity	NPC155011
0.8586	High Similarity	NPC477053
0.8586	High Similarity	NPC477051
0.8586	High Similarity	NPC477052
0.8571	High Similarity	NPC119036
0.8557	High Similarity	NPC42042
0.8557	High Similarity	NPC49371
0.8542	High Similarity	NPC111015
0.8542	High Similarity	NPC166906
0.8529	High Similarity	NPC44063
0.8529	High Similarity	NPC64844
0.8529	High Similarity	NPC263729
0.8529	High Similarity	NPC42847
0.8529	High Similarity	NPC59530
0.8526	High Similarity	NPC189520
0.8526	High Similarity	NPC23434
0.8526	High Similarity	NPC154101
0.8526	High Similarity	NPC26888
0.8515	High Similarity	NPC201763
0.8511	High Similarity	NPC476733
0.8511	High Similarity	NPC215029
0.8511	High Similarity	NPC128496
0.8495	Intermediate Similarity	NPC159046
0.8495	Intermediate Similarity	NPC233836
0.8495	Intermediate Similarity	NPC187376
0.8469	Intermediate Similarity	NPC57416
0.8469	Intermediate Similarity	NPC107243
0.8462	Intermediate Similarity	NPC477852
0.8454	Intermediate Similarity	NPC472485
0.8454	Intermediate Similarity	NPC184848
0.8454	Intermediate Similarity	NPC69548
0.8454	Intermediate Similarity	NPC45324
0.8454	Intermediate Similarity	NPC473240
0.8454	Intermediate Similarity	NPC222845
0.8454	Intermediate Similarity	NPC162001
0.8447	Intermediate Similarity	NPC472218
0.8447	Intermediate Similarity	NPC472219
0.8447	Intermediate Similarity	NPC163216
0.8447	Intermediate Similarity	NPC472217
0.8438	Intermediate Similarity	NPC107674
0.8438	Intermediate Similarity	NPC170220
0.8438	Intermediate Similarity	NPC470224
0.8438	Intermediate Similarity	NPC141497
0.8431	Intermediate Similarity	NPC149047
0.8421	Intermediate Similarity	NPC469400
0.8421	Intermediate Similarity	NPC111585
0.8421	Intermediate Similarity	NPC148414
0.8421	Intermediate Similarity	NPC175628
0.8416	Intermediate Similarity	NPC36688
0.8411	Intermediate Similarity	NPC270958
0.8404	Intermediate Similarity	NPC193360
0.8396	Intermediate Similarity	NPC250109
0.8396	Intermediate Similarity	NPC202889
0.8396	Intermediate Similarity	NPC962
0.8387	Intermediate Similarity	NPC55309
0.8387	Intermediate Similarity	NPC474970
0.8387	Intermediate Similarity	NPC28252
0.8384	Intermediate Similarity	NPC477813
0.8384	Intermediate Similarity	NPC58942
0.8384	Intermediate Similarity	NPC260149
0.8384	Intermediate Similarity	NPC186810
0.8367	Intermediate Similarity	NPC96859
0.8367	Intermediate Similarity	NPC476327
0.8367	Intermediate Similarity	NPC253115
0.8367	Intermediate Similarity	NPC95565
0.8367	Intermediate Similarity	NPC234564
0.8367	Intermediate Similarity	NPC328162
0.8367	Intermediate Similarity	NPC305483
0.8367	Intermediate Similarity	NPC304899
0.8367	Intermediate Similarity	NPC476318
0.8365	Intermediate Similarity	NPC2766
0.8365	Intermediate Similarity	NPC258543
0.8365	Intermediate Similarity	NPC170221
0.8365	Intermediate Similarity	NPC472216
0.8365	Intermediate Similarity	NPC284828
0.8365	Intermediate Similarity	NPC5475
0.8365	Intermediate Similarity	NPC285298
0.8365	Intermediate Similarity	NPC257082
0.8365	Intermediate Similarity	NPC241927
0.8365	Intermediate Similarity	NPC10064
0.8365	Intermediate Similarity	NPC173905
0.8351	Intermediate Similarity	NPC470958
0.8351	Intermediate Similarity	NPC245972
0.8351	Intermediate Similarity	NPC196485
0.8351	Intermediate Similarity	NPC470957
0.835	Intermediate Similarity	NPC475060
0.835	Intermediate Similarity	NPC165873
0.835	Intermediate Similarity	NPC220229
0.8333	Intermediate Similarity	NPC110657
0.8333	Intermediate Similarity	NPC472228
0.8333	Intermediate Similarity	NPC235889
0.8333	Intermediate Similarity	NPC204833
0.8333	Intermediate Similarity	NPC86266
0.8333	Intermediate Similarity	NPC212301
0.8333	Intermediate Similarity	NPC297265
0.8333	Intermediate Similarity	NPC209502
0.8333	Intermediate Similarity	NPC28656
0.8333	Intermediate Similarity	NPC96268
0.8333	Intermediate Similarity	NPC472227
0.8317	Intermediate Similarity	NPC473928
0.8317	Intermediate Similarity	NPC185530
0.8317	Intermediate Similarity	NPC473788
0.8317	Intermediate Similarity	NPC136289
0.8317	Intermediate Similarity	NPC475558
0.8316	Intermediate Similarity	NPC84271
0.8316	Intermediate Similarity	NPC474245
0.8316	Intermediate Similarity	NPC186688
0.8316	Intermediate Similarity	NPC32830
0.8316	Intermediate Similarity	NPC76879
0.8316	Intermediate Similarity	NPC77168
0.8316	Intermediate Similarity	NPC474889
0.8316	Intermediate Similarity	NPC102414
0.83	Intermediate Similarity	NPC110149
0.83	Intermediate Similarity	NPC316964
0.83	Intermediate Similarity	NPC144956
0.83	Intermediate Similarity	NPC154072
0.8286	Intermediate Similarity	NPC5284
0.8286	Intermediate Similarity	NPC6206
0.8283	Intermediate Similarity	NPC475032
0.8283	Intermediate Similarity	NPC475033
0.8283	Intermediate Similarity	NPC189880
0.8283	Intermediate Similarity	NPC320306
0.8283	Intermediate Similarity	NPC18509
0.8269	Intermediate Similarity	NPC217201
0.8265	Intermediate Similarity	NPC266899
0.8257	Intermediate Similarity	NPC118638
0.8252	Intermediate Similarity	NPC48733
0.8252	Intermediate Similarity	NPC323834
0.8252	Intermediate Similarity	NPC319077
0.8252	Intermediate Similarity	NPC150531
0.8252	Intermediate Similarity	NPC97202
0.8252	Intermediate Similarity	NPC202167
0.8252	Intermediate Similarity	NPC296945
0.8252	Intermediate Similarity	NPC257353
0.8252	Intermediate Similarity	NPC49958
0.8252	Intermediate Similarity	NPC214264
0.8252	Intermediate Similarity	NPC50692
0.8252	Intermediate Similarity	NPC302607
0.8252	Intermediate Similarity	NPC181265
0.8252	Intermediate Similarity	NPC260268
0.8252	Intermediate Similarity	NPC476027
0.8252	Intermediate Similarity	NPC85829
0.8252	Intermediate Similarity	NPC152695
0.8252	Intermediate Similarity	NPC475571
0.8252	Intermediate Similarity	NPC171137
0.8247	Intermediate Similarity	NPC224060
0.8247	Intermediate Similarity	NPC244356
0.8241	Intermediate Similarity	NPC49492
0.8241	Intermediate Similarity	NPC266728
0.8241	Intermediate Similarity	NPC148458
0.8235	Intermediate Similarity	NPC236390
0.8235	Intermediate Similarity	NPC312900
0.8235	Intermediate Similarity	NPC55872
0.8235	Intermediate Similarity	NPC159442
0.8235	Intermediate Similarity	NPC26478
0.8229	Intermediate Similarity	NPC289213
0.8229	Intermediate Similarity	NPC20388
0.8229	Intermediate Similarity	NPC320026
0.8224	Intermediate Similarity	NPC52634

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 NPC477854 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	1472
0.2-0.3	3919
0.3-0.4	2391
0.4-0.5	675
0.5-0.6	182
0.6-0.7	160
0.7-0.8	136
0.8-0.85	50
0.85-0.9	10
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8627	High Similarity	NPD6881	Approved
0.8627	High Similarity	NPD6899	Approved
0.8614	High Similarity	NPD6402	Approved
0.8614	High Similarity	NPD5739	Approved
0.8614	High Similarity	NPD6675	Approved
0.8614	High Similarity	NPD7128	Approved
0.8529	High Similarity	NPD5697	Approved
0.8462	Intermediate Similarity	NPD7290	Approved
0.8462	Intermediate Similarity	NPD7102	Approved
0.8462	Intermediate Similarity	NPD6883	Approved
0.8447	Intermediate Similarity	NPD6011	Approved
0.8447	Intermediate Similarity	NPD7320	Approved
0.8396	Intermediate Similarity	NPD4632	Approved
0.8381	Intermediate Similarity	NPD6617	Approved
0.8381	Intermediate Similarity	NPD8130	Phase 1
0.8381	Intermediate Similarity	NPD6847	Approved
0.8381	Intermediate Similarity	NPD6649	Approved
0.8381	Intermediate Similarity	NPD6650	Approved
0.8381	Intermediate Similarity	NPD6869	Approved
0.8365	Intermediate Similarity	NPD6013	Approved
0.8365	Intermediate Similarity	NPD6014	Approved
0.8365	Intermediate Similarity	NPD6373	Approved
0.8365	Intermediate Similarity	NPD6372	Approved
0.8365	Intermediate Similarity	NPD6012	Approved
0.835	Intermediate Similarity	NPD5701	Approved
0.8333	Intermediate Similarity	NPD6079	Approved
0.8316	Intermediate Similarity	NPD5328	Approved
0.8302	Intermediate Similarity	NPD8297	Approved
0.8302	Intermediate Similarity	NPD6882	Approved
0.83	Intermediate Similarity	NPD5286	Approved
0.83	Intermediate Similarity	NPD4696	Approved
0.83	Intermediate Similarity	NPD5285	Approved
0.8283	Intermediate Similarity	NPD4755	Approved
0.8252	Intermediate Similarity	NPD6008	Approved
0.8247	Intermediate Similarity	NPD6399	Phase 3
0.8218	Intermediate Similarity	NPD5223	Approved
0.8208	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8172	Intermediate Similarity	NPD4786	Approved
0.8165	Intermediate Similarity	NPD6009	Approved
0.8137	Intermediate Similarity	NPD5211	Phase 2
0.8137	Intermediate Similarity	NPD5225	Approved
0.8137	Intermediate Similarity	NPD5224	Approved
0.8137	Intermediate Similarity	NPD5226	Approved
0.8137	Intermediate Similarity	NPD4633	Approved
0.8119	Intermediate Similarity	NPD4700	Approved
0.81	Intermediate Similarity	NPD6084	Phase 2
0.81	Intermediate Similarity	NPD6083	Phase 2
0.8061	Intermediate Similarity	NPD4202	Approved
0.8058	Intermediate Similarity	NPD5175	Approved
0.8058	Intermediate Similarity	NPD5174	Approved
0.802	Intermediate Similarity	NPD7638	Approved
0.8	Intermediate Similarity	NPD5222	Approved
0.8	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5221	Approved
0.7981	Intermediate Similarity	NPD5141	Approved
0.7957	Intermediate Similarity	NPD3667	Approved
0.7946	Intermediate Similarity	NPD6319	Approved
0.7944	Intermediate Similarity	NPD4634	Approved
0.7941	Intermediate Similarity	NPD7640	Approved
0.7941	Intermediate Similarity	NPD7639	Approved
0.7928	Intermediate Similarity	NPD6335	Approved
0.7921	Intermediate Similarity	NPD5173	Approved
0.7895	Intermediate Similarity	NPD7604	Phase 2
0.7895	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD4754	Approved
0.7876	Intermediate Similarity	NPD5983	Phase 2
0.7857	Intermediate Similarity	NPD7101	Approved
0.7857	Intermediate Similarity	NPD7100	Approved
0.7838	Intermediate Similarity	NPD6317	Approved
0.7826	Intermediate Similarity	NPD7492	Approved
0.7822	Intermediate Similarity	NPD4697	Phase 3
0.7812	Intermediate Similarity	NPD3618	Phase 1
0.7812	Intermediate Similarity	NPD6409	Approved
0.7812	Intermediate Similarity	NPD7146	Approved
0.7812	Intermediate Similarity	NPD6684	Approved
0.7812	Intermediate Similarity	NPD5330	Approved
0.7812	Intermediate Similarity	NPD7334	Approved
0.7812	Intermediate Similarity	NPD7521	Approved
0.7789	Intermediate Similarity	NPD3666	Approved
0.7789	Intermediate Similarity	NPD3133	Approved
0.7789	Intermediate Similarity	NPD3665	Phase 1
0.7788	Intermediate Similarity	NPD6054	Approved
0.7778	Intermediate Similarity	NPD7515	Phase 2
0.7768	Intermediate Similarity	NPD6313	Approved
0.7768	Intermediate Similarity	NPD6314	Approved
0.7759	Intermediate Similarity	NPD6336	Discontinued
0.7759	Intermediate Similarity	NPD6616	Approved
0.7757	Intermediate Similarity	NPD4730	Approved
0.7757	Intermediate Similarity	NPD4729	Approved
0.7755	Intermediate Similarity	NPD4753	Phase 2
0.7748	Intermediate Similarity	NPD6274	Approved
0.7736	Intermediate Similarity	NPD4767	Approved
0.7736	Intermediate Similarity	NPD4768	Approved
0.7723	Intermediate Similarity	NPD5695	Phase 3
0.7723	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD6697	Approved
0.7717	Intermediate Similarity	NPD6115	Approved
0.7717	Intermediate Similarity	NPD6114	Approved
0.7717	Intermediate Similarity	NPD6118	Approved
0.7692	Intermediate Similarity	NPD7078	Approved
0.767	Intermediate Similarity	NPD5696	Approved
0.7653	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD6903	Approved
0.7652	Intermediate Similarity	NPD6370	Approved
0.7632	Intermediate Similarity	NPD6059	Approved
0.7629	Intermediate Similarity	NPD6098	Approved
0.7627	Intermediate Similarity	NPD7736	Approved
0.7624	Intermediate Similarity	NPD7748	Approved
0.7615	Intermediate Similarity	NPD5247	Approved
0.7615	Intermediate Similarity	NPD5135	Approved
0.7615	Intermediate Similarity	NPD5169	Approved
0.7615	Intermediate Similarity	NPD5248	Approved
0.7615	Intermediate Similarity	NPD5251	Approved
0.7615	Intermediate Similarity	NPD5250	Approved
0.7615	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD5249	Phase 3
0.76	Intermediate Similarity	NPD5281	Approved
0.76	Intermediate Similarity	NPD8035	Phase 2
0.76	Intermediate Similarity	NPD5284	Approved
0.76	Intermediate Similarity	NPD6411	Approved
0.76	Intermediate Similarity	NPD8034	Phase 2
0.7593	Intermediate Similarity	NPD5128	Approved
0.7589	Intermediate Similarity	NPD6868	Approved
0.7579	Intermediate Similarity	NPD4221	Approved
0.7579	Intermediate Similarity	NPD4223	Phase 3
0.7576	Intermediate Similarity	NPD6080	Approved
0.7576	Intermediate Similarity	NPD6673	Approved
0.7576	Intermediate Similarity	NPD6904	Approved
0.7565	Intermediate Similarity	NPD6016	Approved
0.7565	Intermediate Similarity	NPD6015	Approved
0.7565	Intermediate Similarity	NPD6909	Approved
0.7565	Intermediate Similarity	NPD6908	Approved
0.7565	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD7525	Registered
0.7549	Intermediate Similarity	NPD4629	Approved
0.7549	Intermediate Similarity	NPD5210	Approved
0.7545	Intermediate Similarity	NPD5127	Approved
0.7545	Intermediate Similarity	NPD5216	Approved
0.7545	Intermediate Similarity	NPD5217	Approved
0.7545	Intermediate Similarity	NPD5215	Approved
0.7542	Intermediate Similarity	NPD8293	Discontinued
0.7526	Intermediate Similarity	NPD5329	Approved
0.7522	Intermediate Similarity	NPD7115	Discovery
0.75	Intermediate Similarity	NPD6117	Approved
0.75	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5988	Approved
0.7477	Intermediate Similarity	NPD6053	Discontinued
0.7475	Intermediate Similarity	NPD6672	Approved
0.7475	Intermediate Similarity	NPD5737	Approved
0.7474	Intermediate Similarity	NPD5369	Approved
0.7458	Intermediate Similarity	NPD7507	Approved
0.7423	Intermediate Similarity	NPD4197	Approved
0.7423	Intermediate Similarity	NPD3668	Phase 3
0.7419	Intermediate Similarity	NPD6116	Phase 1
0.7404	Intermediate Similarity	NPD7902	Approved
0.74	Intermediate Similarity	NPD6101	Approved
0.74	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6435	Approved
0.7391	Intermediate Similarity	NPD6942	Approved
0.7391	Intermediate Similarity	NPD7339	Approved
0.7374	Intermediate Similarity	NPD3573	Approved
0.7374	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5368	Approved
0.7353	Intermediate Similarity	NPD5778	Approved
0.7353	Intermediate Similarity	NPD5779	Approved
0.7345	Intermediate Similarity	NPD5167	Approved
0.7339	Intermediate Similarity	NPD6412	Phase 2
0.732	Intermediate Similarity	NPD4788	Approved
0.732	Intermediate Similarity	NPD5362	Discontinued
0.73	Intermediate Similarity	NPD5208	Approved
0.729	Intermediate Similarity	NPD7632	Discontinued
0.7283	Intermediate Similarity	NPD4784	Approved
0.7283	Intermediate Similarity	NPD4785	Approved
0.7283	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6001	Approved
0.7273	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4138	Approved
0.7273	Intermediate Similarity	NPD4690	Approved
0.7273	Intermediate Similarity	NPD4693	Phase 3
0.7273	Intermediate Similarity	NPD5168	Approved
0.7273	Intermediate Similarity	NPD7319	Approved
0.7273	Intermediate Similarity	NPD4688	Approved
0.7273	Intermediate Similarity	NPD5690	Phase 2
0.7273	Intermediate Similarity	NPD5786	Approved
0.7273	Intermediate Similarity	NPD5205	Approved
0.7273	Intermediate Similarity	NPD4689	Approved
0.7255	Intermediate Similarity	NPD6050	Approved
0.7255	Intermediate Similarity	NPD5694	Approved
0.7255	Intermediate Similarity	NPD7637	Suspended
0.7255	Intermediate Similarity	NPD5693	Phase 1
0.7228	Intermediate Similarity	NPD6051	Approved
0.7204	Intermediate Similarity	NPD3702	Approved
0.7204	Intermediate Similarity	NPD3703	Phase 2
0.719	Intermediate Similarity	NPD6033	Approved
0.7158	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5692	Phase 3
0.7157	Intermediate Similarity	NPD5207	Approved
0.7117	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7900	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