NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	458.38
Volume:	514.308
LogP:	7.448
LogD:	5.21
LogS:	-6.299
# Rotatable Bonds:	6
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.242
Synthetic Accessibility Score:	5.076
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.748
MDCK Permeability:	1.3873199350200593e-05
Pgp-inhibitor:	0.962
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.95
30% Bioavailability (F30%):	0.33

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.266
Plasma Protein Binding (PPB):	98.12984466552734%
Volume Distribution (VD):	1.483
Pgp-substrate:	2.9215455055236816%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.452
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.21
CYP2C9-substrate:	0.283
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.398
CYP3A4-inhibitor:	0.92
CYP3A4-substrate:	0.554

ADMET: Excretion

Clearance (CL):	13.618
Half-life (T1/2):	0.013

ADMET: Toxicity

hERG Blockers:	0.163
Human Hepatotoxicity (H-HT):	0.356
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.815
Maximum Recommended Daily Dose:	0.902
Skin Sensitization:	0.115
Carcinogencity:	0.69
Eye Corrosion:	0.113
Eye Irritation:	0.023
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC477514

Natural Product ID:	NPC477514
*Common Name:**	(5S,9R,10S,13S,14S,16S,17S)-17-[(2R)-5-hydroperoxy-6-methylhept-6-en-2-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-16-ol
IUPAC Name:	(5S,9R,10S,13S,14S,16S,17S)-17-[(2R)-5-hydroperoxy-6-methylhept-6-en-2-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-16-ol
Synonyms:	Meliasenin K
Standard InCHIKey:	FRZPGQFZKQIUFW-ZPOOIBIBSA-N
Standard InCHI:	InChI=1S/C30H50O3/c1-19(2)24(33-32)12-10-20(3)26-23(31)18-30(8)22-11-13-25-27(4,5)15-9-16-28(25,6)21(22)14-17-29(26,30)7/h11,20-21,23-26,31-32H,1,9-10,12-18H2,2-8H3/t20-,21+,23+,24?,25+,26-,28-,29+,30-/m1/s1
SMILES:	C[C@H](CCC(C(=C)C)OO)[C@@H]1[C@H](C[C@]2([C@]1(CC[C@H]3C2=CC[C@@H]4[C@@]3(CCCC4(C)C)C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	53320492
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19341288]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20961091]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	fruits	Wanyuan County, Sichuan Province, China	2007-OCT	PMID[20961091]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
NPT1045	Cell Line	U2OS	Homo sapiens	IC50	=	7.2	ug/ml	PMID[20961091]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2.4	ug/ml	PMID[20961091]

☑ 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 NPC477514 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	148
0.1-0.2	1348
0.2-0.3	8704
0.3-0.4	14887
0.4-0.5	6718
0.5-0.6	5726
0.6-0.7	3799
0.7-0.8	1065
0.8-0.85	190
0.85-0.9	70
0.9-0.95	41
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9459	High Similarity	NPC477522
0.9459	High Similarity	NPC473943
0.9333	High Similarity	NPC1319
0.9211	High Similarity	NPC26117
0.92	High Similarity	NPC474216
0.9189	High Similarity	NPC321016
0.9189	High Similarity	NPC321381
0.9189	High Similarity	NPC247325
0.9189	High Similarity	NPC96319
0.9189	High Similarity	NPC244488
0.9189	High Similarity	NPC107059
0.9114	High Similarity	NPC318390
0.9091	High Similarity	NPC47761
0.9079	High Similarity	NPC28862
0.9079	High Similarity	NPC47982
0.9079	High Similarity	NPC143182
0.9079	High Similarity	NPC84694
0.9079	High Similarity	NPC209430
0.9079	High Similarity	NPC30986
0.9079	High Similarity	NPC81306
0.9079	High Similarity	NPC109546
0.9067	High Similarity	NPC318495
0.9067	High Similarity	NPC155986
0.9067	High Similarity	NPC198968
0.9054	High Similarity	NPC136188
0.9054	High Similarity	NPC134847
0.9054	High Similarity	NPC22105
0.9054	High Similarity	NPC230301
0.9054	High Similarity	NPC304309
0.9054	High Similarity	NPC471723
0.9054	High Similarity	NPC141071
0.9054	High Similarity	NPC257347
0.9054	High Similarity	NPC28657
0.9054	High Similarity	NPC288035
0.9054	High Similarity	NPC285893
0.9054	High Similarity	NPC162742
0.9041	High Similarity	NPC474140
0.8974	High Similarity	NPC470614
0.8974	High Similarity	NPC1272
0.8961	High Similarity	NPC234193
0.8961	High Similarity	NPC164840
0.8961	High Similarity	NPC209944
0.8961	High Similarity	NPC241290
0.8947	High Similarity	NPC87604
0.8933	High Similarity	NPC189883
0.8933	High Similarity	NPC129165
0.8933	High Similarity	NPC240604
0.8933	High Similarity	NPC300324
0.8933	High Similarity	NPC113733
0.8933	High Similarity	NPC134330
0.8889	High Similarity	NPC317590
0.8846	High Similarity	NPC209620
0.8846	High Similarity	NPC474759
0.8846	High Similarity	NPC23852
0.8846	High Similarity	NPC82986
0.8846	High Similarity	NPC474731
0.8846	High Similarity	NPC474683
0.8846	High Similarity	NPC264245
0.8846	High Similarity	NPC7505
0.8846	High Similarity	NPC474752
0.8831	High Similarity	NPC328714
0.8816	High Similarity	NPC214570
0.8816	High Similarity	NPC34019
0.8784	High Similarity	NPC472506
0.8765	High Similarity	NPC469994
0.8765	High Similarity	NPC293287
0.8765	High Similarity	NPC152808
0.875	High Similarity	NPC209802
0.875	High Similarity	NPC82902
0.875	High Similarity	NPC124172
0.875	High Similarity	NPC160209
0.8734	High Similarity	NPC470049
0.8734	High Similarity	NPC189972
0.8734	High Similarity	NPC201852
0.8734	High Similarity	NPC49964
0.8734	High Similarity	NPC101462
0.8734	High Similarity	NPC20853
0.8734	High Similarity	NPC50964
0.8718	High Similarity	NPC236112
0.8701	High Similarity	NPC285761
0.8701	High Similarity	NPC18603
0.8701	High Similarity	NPC76931
0.8701	High Similarity	NPC275910
0.8701	High Similarity	NPC244385
0.8701	High Similarity	NPC6978
0.8701	High Similarity	NPC138621
0.8701	High Similarity	NPC307965
0.8701	High Similarity	NPC167037
0.8684	High Similarity	NPC202642
0.8684	High Similarity	NPC237460
0.8684	High Similarity	NPC470362
0.8684	High Similarity	NPC46160
0.8684	High Similarity	NPC73875
0.8667	High Similarity	NPC469534
0.8667	High Similarity	NPC469533
0.8667	High Similarity	NPC469593
0.8649	High Similarity	NPC164045
0.8642	High Similarity	NPC474349
0.8642	High Similarity	NPC474189
0.8642	High Similarity	NPC474218
0.8625	High Similarity	NPC475789
0.8625	High Similarity	NPC474634
0.8625	High Similarity	NPC477818
0.8625	High Similarity	NPC317458
0.8625	High Similarity	NPC110778
0.8608	High Similarity	NPC474531
0.8608	High Similarity	NPC6434
0.8608	High Similarity	NPC470383
0.859	High Similarity	NPC273410
0.859	High Similarity	NPC80530
0.8571	High Similarity	NPC320026
0.8553	High Similarity	NPC118508
0.8553	High Similarity	NPC121744
0.8553	High Similarity	NPC322353
0.8537	High Similarity	NPC24277
0.8533	High Similarity	NPC471799
0.8519	High Similarity	NPC474047
0.8519	High Similarity	NPC205845
0.8519	High Similarity	NPC470077
0.8519	High Similarity	NPC185568
0.8514	High Similarity	NPC475728
0.8514	High Similarity	NPC34834
0.85	High Similarity	NPC87489
0.85	High Similarity	NPC296701
0.85	High Similarity	NPC218616
0.85	High Similarity	NPC202389
0.85	High Similarity	NPC5985
0.85	High Similarity	NPC30166
0.8481	Intermediate Similarity	NPC13554
0.8481	Intermediate Similarity	NPC322313
0.8481	Intermediate Similarity	NPC236237
0.8481	Intermediate Similarity	NPC102253
0.8462	Intermediate Similarity	NPC302041
0.8462	Intermediate Similarity	NPC205455
0.8462	Intermediate Similarity	NPC65897
0.8462	Intermediate Similarity	NPC85346
0.8462	Intermediate Similarity	NPC186191
0.8452	Intermediate Similarity	NPC2983
0.8442	Intermediate Similarity	NPC38141
0.8421	Intermediate Similarity	NPC329090
0.8421	Intermediate Similarity	NPC27395
0.8421	Intermediate Similarity	NPC471797
0.8415	Intermediate Similarity	NPC266511
0.8415	Intermediate Similarity	NPC274448
0.8415	Intermediate Similarity	NPC157257
0.8415	Intermediate Similarity	NPC471224
0.84	Intermediate Similarity	NPC242001
0.8395	Intermediate Similarity	NPC141941
0.8395	Intermediate Similarity	NPC193870
0.8395	Intermediate Similarity	NPC134481
0.8395	Intermediate Similarity	NPC470384
0.8356	Intermediate Similarity	NPC197805
0.8354	Intermediate Similarity	NPC49599
0.8354	Intermediate Similarity	NPC49627
0.8333	Intermediate Similarity	NPC477009
0.8333	Intermediate Similarity	NPC470542
0.8333	Intermediate Similarity	NPC471952
0.8333	Intermediate Similarity	NPC328313
0.8333	Intermediate Similarity	NPC138502
0.8333	Intermediate Similarity	NPC307336
0.8333	Intermediate Similarity	NPC238352
0.8333	Intermediate Similarity	NPC260301
0.8333	Intermediate Similarity	NPC91594
0.8313	Intermediate Similarity	NPC261266
0.8313	Intermediate Similarity	NPC201273
0.8313	Intermediate Similarity	NPC6391
0.8313	Intermediate Similarity	NPC139724
0.8312	Intermediate Similarity	NPC471468
0.8312	Intermediate Similarity	NPC319090
0.8312	Intermediate Similarity	NPC328104
0.8312	Intermediate Similarity	NPC185536
0.8293	Intermediate Similarity	NPC59453
0.8293	Intermediate Similarity	NPC33913
0.8293	Intermediate Similarity	NPC85774
0.8293	Intermediate Similarity	NPC238485
0.8293	Intermediate Similarity	NPC475798
0.8293	Intermediate Similarity	NPC214043
0.8293	Intermediate Similarity	NPC58841
0.8293	Intermediate Similarity	NPC321187
0.8293	Intermediate Similarity	NPC329043
0.8293	Intermediate Similarity	NPC478102
0.8293	Intermediate Similarity	NPC161423
0.8293	Intermediate Similarity	NPC227064
0.8293	Intermediate Similarity	NPC221758
0.8293	Intermediate Similarity	NPC127606
0.8293	Intermediate Similarity	NPC472265
0.8293	Intermediate Similarity	NPC231310
0.8289	Intermediate Similarity	NPC201373
0.8289	Intermediate Similarity	NPC182717
0.8289	Intermediate Similarity	NPC474743
0.8272	Intermediate Similarity	NPC248886
0.8267	Intermediate Similarity	NPC145498
0.8243	Intermediate Similarity	NPC208999
0.8235	Intermediate Similarity	NPC473647
0.8235	Intermediate Similarity	NPC105495
0.8235	Intermediate Similarity	NPC76879
0.8235	Intermediate Similarity	NPC477943
0.8228	Intermediate Similarity	NPC312328
0.8228	Intermediate Similarity	NPC318136
0.8228	Intermediate Similarity	NPC475

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 NPC477514 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1593
0.2-0.3	4588
0.3-0.4	2003
0.4-0.5	390
0.5-0.6	147
0.6-0.7	166
0.7-0.8	89
0.8-0.85	22
0.85-0.9	4
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9189	High Similarity	NPD3701	Clinical (unspecified phase)
0.9054	High Similarity	NPD6942	Approved
0.9054	High Similarity	NPD7339	Approved
0.8904	High Similarity	NPD4243	Approved
0.8667	High Similarity	NPD4784	Approved
0.8667	High Similarity	NPD4785	Approved
0.8481	Intermediate Similarity	NPD7525	Registered
0.8434	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD6926	Approved
0.8421	Intermediate Similarity	NPD6924	Approved
0.8312	Intermediate Similarity	NPD4190	Phase 3
0.8312	Intermediate Similarity	NPD5275	Approved
0.8293	Intermediate Similarity	NPD3133	Approved
0.8293	Intermediate Similarity	NPD3665	Phase 1
0.8293	Intermediate Similarity	NPD3666	Approved
0.8293	Intermediate Similarity	NPD4786	Approved
0.8205	Intermediate Similarity	NPD6933	Approved
0.8133	Intermediate Similarity	NPD6922	Approved
0.8133	Intermediate Similarity	NPD6923	Approved
0.8125	Intermediate Similarity	NPD6929	Approved
0.8125	Intermediate Similarity	NPD4195	Approved
0.8049	Intermediate Similarity	NPD3667	Approved
0.8026	Intermediate Similarity	NPD7143	Approved
0.8026	Intermediate Similarity	NPD7144	Approved
0.8025	Intermediate Similarity	NPD4748	Discontinued
0.8025	Intermediate Similarity	NPD6931	Approved
0.8025	Intermediate Similarity	NPD6930	Phase 2
0.7922	Intermediate Similarity	NPD7150	Approved
0.7922	Intermediate Similarity	NPD7151	Approved
0.7922	Intermediate Similarity	NPD7152	Approved
0.7901	Intermediate Similarity	NPD7645	Phase 2
0.7875	Intermediate Similarity	NPD6925	Approved
0.7875	Intermediate Similarity	NPD5776	Phase 2
0.7831	Intermediate Similarity	NPD4221	Approved
0.7831	Intermediate Similarity	NPD4223	Phase 3
0.7816	Intermediate Similarity	NPD4753	Phase 2
0.7816	Intermediate Similarity	NPD5328	Approved
0.7778	Intermediate Similarity	NPD7145	Approved
0.7765	Intermediate Similarity	NPD5329	Approved
0.7753	Intermediate Similarity	NPD4202	Approved
0.7738	Intermediate Similarity	NPD6695	Phase 3
0.7674	Intermediate Similarity	NPD3618	Phase 1
0.7654	Intermediate Similarity	NPD6932	Approved
0.7647	Intermediate Similarity	NPD4197	Approved
0.7647	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6079	Approved
0.7614	Intermediate Similarity	NPD6051	Approved
0.759	Intermediate Similarity	NPD7509	Discontinued
0.759	Intermediate Similarity	NPD7514	Phase 3
0.7561	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6893	Approved
0.7529	Intermediate Similarity	NPD4788	Approved
0.75	Intermediate Similarity	NPD6902	Approved
0.7471	Intermediate Similarity	NPD4688	Approved
0.7471	Intermediate Similarity	NPD4693	Phase 3
0.7471	Intermediate Similarity	NPD7146	Approved
0.7471	Intermediate Similarity	NPD5279	Phase 3
0.7471	Intermediate Similarity	NPD5205	Approved
0.7471	Intermediate Similarity	NPD4690	Approved
0.7471	Intermediate Similarity	NPD7521	Approved
0.7471	Intermediate Similarity	NPD7334	Approved
0.7471	Intermediate Similarity	NPD4138	Approved
0.7471	Intermediate Similarity	NPD4689	Approved
0.7471	Intermediate Similarity	NPD6409	Approved
0.7471	Intermediate Similarity	NPD6684	Approved
0.7471	Intermediate Similarity	NPD5330	Approved
0.747	Intermediate Similarity	NPD6683	Phase 2
0.7419	Intermediate Similarity	NPD6083	Phase 2
0.7419	Intermediate Similarity	NPD6084	Phase 2
0.7419	Intermediate Similarity	NPD4755	Approved
0.7391	Intermediate Similarity	NPD4629	Approved
0.7391	Intermediate Similarity	NPD5210	Approved
0.7386	Intermediate Similarity	NPD7524	Approved
0.7386	Intermediate Similarity	NPD7750	Discontinued
0.7381	Intermediate Similarity	NPD7332	Phase 2
0.7363	Intermediate Similarity	NPD6399	Phase 3
0.7303	Intermediate Similarity	NPD4723	Approved
0.7303	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4722	Approved
0.7303	Intermediate Similarity	NPD6903	Approved
0.7294	Intermediate Similarity	NPD6898	Phase 1
0.7292	Intermediate Similarity	NPD5211	Phase 2
0.7273	Intermediate Similarity	NPD5280	Approved
0.7273	Intermediate Similarity	NPD5690	Phase 2
0.7273	Intermediate Similarity	NPD4694	Approved
0.7263	Intermediate Similarity	NPD5286	Approved
0.7263	Intermediate Similarity	NPD4700	Approved
0.7263	Intermediate Similarity	NPD4696	Approved
0.7263	Intermediate Similarity	NPD5285	Approved
0.7241	Intermediate Similarity	NPD3668	Phase 3
0.7195	Intermediate Similarity	NPD8264	Approved
0.7188	Intermediate Similarity	NPD5223	Approved
0.7159	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7638	Approved
0.7143	Intermediate Similarity	NPD5141	Approved
0.7128	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5222	Approved
0.7128	Intermediate Similarity	NPD5221	Approved
0.7128	Intermediate Similarity	NPD4697	Phase 3
0.7125	Intermediate Similarity	NPD4787	Phase 1
0.7113	Intermediate Similarity	NPD5225	Approved
0.7113	Intermediate Similarity	NPD4633	Approved
0.7113	Intermediate Similarity	NPD5224	Approved
0.7113	Intermediate Similarity	NPD5226	Approved
0.7093	Intermediate Similarity	NPD4139	Approved
0.7093	Intermediate Similarity	NPD4692	Approved
0.7083	Intermediate Similarity	NPD7639	Approved
0.7083	Intermediate Similarity	NPD7640	Approved
0.7079	Intermediate Similarity	NPD6098	Approved
0.7071	Intermediate Similarity	NPD6675	Approved
0.7071	Intermediate Similarity	NPD6402	Approved
0.7071	Intermediate Similarity	NPD7128	Approved
0.7071	Intermediate Similarity	NPD5739	Approved
0.7065	Intermediate Similarity	NPD7087	Discontinued
0.7053	Intermediate Similarity	NPD5173	Approved
0.7041	Intermediate Similarity	NPD5175	Approved
0.7041	Intermediate Similarity	NPD5174	Approved
0.7041	Intermediate Similarity	NPD4754	Approved
0.7021	Intermediate Similarity	NPD5695	Phase 3
0.6979	Remote Similarity	NPD5696	Approved
0.6941	Remote Similarity	NPD3617	Approved
0.6931	Remote Similarity	NPD6899	Approved
0.6931	Remote Similarity	NPD6881	Approved
0.6931	Remote Similarity	NPD7320	Approved
0.6923	Remote Similarity	NPD6672	Approved
0.6923	Remote Similarity	NPD5737	Approved
0.6914	Remote Similarity	NPD4245	Approved
0.6914	Remote Similarity	NPD4244	Approved
0.69	Remote Similarity	NPD4767	Approved
0.69	Remote Similarity	NPD4768	Approved
0.6889	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7515	Phase 2
0.6882	Remote Similarity	NPD5281	Approved
0.6882	Remote Similarity	NPD5284	Approved
0.6863	Remote Similarity	NPD6373	Approved
0.6863	Remote Similarity	NPD6372	Approved
0.6848	Remote Similarity	NPD6673	Approved
0.6848	Remote Similarity	NPD6904	Approved
0.6848	Remote Similarity	NPD6080	Approved
0.6832	Remote Similarity	NPD5701	Approved
0.6832	Remote Similarity	NPD5697	Approved
0.6832	Remote Similarity	NPD6412	Phase 2
0.6804	Remote Similarity	NPD5290	Discontinued
0.6796	Remote Similarity	NPD7102	Approved
0.6796	Remote Similarity	NPD6883	Approved
0.6796	Remote Similarity	NPD7290	Approved
0.679	Remote Similarity	NPD3698	Phase 2
0.679	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4096	Approved
0.6765	Remote Similarity	NPD4730	Approved
0.6765	Remote Similarity	NPD6011	Approved
0.6765	Remote Similarity	NPD4729	Approved
0.6765	Remote Similarity	NPD5128	Approved
0.6753	Remote Similarity	NPD368	Approved
0.6739	Remote Similarity	NPD5208	Approved
0.6731	Remote Similarity	NPD6650	Approved
0.6731	Remote Similarity	NPD8130	Phase 1
0.6731	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6617	Approved
0.6731	Remote Similarity	NPD6869	Approved
0.6731	Remote Similarity	NPD6649	Approved
0.6731	Remote Similarity	NPD6847	Approved
0.6707	Remote Similarity	NPD4747	Approved
0.6703	Remote Similarity	NPD4623	Approved
0.6703	Remote Similarity	NPD4519	Discontinued
0.6702	Remote Similarity	NPD7637	Suspended
0.6702	Remote Similarity	NPD5693	Phase 1
0.6699	Remote Similarity	NPD6013	Approved
0.6699	Remote Similarity	NPD6014	Approved
0.6699	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD4159	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5135	Approved
0.6635	Remote Similarity	NPD5250	Approved
0.6635	Remote Similarity	NPD5248	Approved
0.6635	Remote Similarity	NPD5169	Approved
0.6635	Remote Similarity	NPD5249	Phase 3
0.6635	Remote Similarity	NPD4634	Approved
0.6635	Remote Similarity	NPD5247	Approved
0.6635	Remote Similarity	NPD5251	Approved
0.6635	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5133	Approved
0.6627	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD342	Phase 1
0.6596	Remote Similarity	NPD7136	Phase 2
0.6591	Remote Similarity	NPD4695	Discontinued
0.6585	Remote Similarity	NPD4137	Phase 3
0.6571	Remote Similarity	NPD5217	Approved
0.6571	Remote Similarity	NPD5215	Approved
0.6571	Remote Similarity	NPD5216	Approved
0.6571	Remote Similarity	NPD5127	Approved
0.6562	Remote Similarity	NPD5707	Approved
0.6562	Remote Similarity	NPD7748	Approved
0.6559	Remote Similarity	NPD4518	Approved
0.6556	Remote Similarity	NPD5362	Discontinued
0.6556	Remote Similarity	NPD5332	Approved
0.6556	Remote Similarity	NPD5331	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