NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	236.18
Volume:	263.191
LogP:	3.282
LogD:	3.477
LogS:	-3.798
# Rotatable Bonds:	2
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.748
Synthetic Accessibility Score:	4.403
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.458
MDCK Permeability:	2.535948806325905e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.782
30% Bioavailability (F30%):	0.526

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.861
Plasma Protein Binding (PPB):	87.32209014892578%
Volume Distribution (VD):	0.991
Pgp-substrate:	7.249786853790283%

ADMET: Metabolism

CYP1A2-inhibitor:	0.679
CYP1A2-substrate:	0.521
CYP2C19-inhibitor:	0.236
CYP2C19-substrate:	0.814
CYP2C9-inhibitor:	0.204
CYP2C9-substrate:	0.724
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.745
CYP3A4-inhibitor:	0.084
CYP3A4-substrate:	0.34

ADMET: Excretion

Clearance (CL):	6.793
Half-life (T1/2):	0.44

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.505
Drug-inuced Liver Injury (DILI):	0.122
AMES Toxicity:	0.26
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.299
Skin Sensitization:	0.945
Carcinogencity:	0.731
Eye Corrosion:	0.964
Eye Irritation:	0.972
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC472301

Natural Product ID:	NPC472301
*Common Name:**	YRHFMDFGYQELMG-UQOMUDLDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YRHFMDFGYQELMG-UQOMUDLDSA-N
Standard InCHI:	InChI=1S/C15H24O2/c1-10(2)13-6-4-11(3)14-7-5-12(9-16)8-15(13,14)17/h8-11,13-14,17H,4-7H2,1-3H3/t11-,13+,14+,15-/m1/s1
SMILES:	CC1CCC(C2(C1CCC(=C2)C=O)O)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3358069
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32931	pterolobium macropterum	Species	Fabaceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[25337628]

☑ 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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	88770.0	nM	PMID[447433]

☑ 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 NPC472301 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	167
0.1-0.2	1124
0.2-0.3	4888
0.3-0.4	12528
0.4-0.5	12494
0.5-0.6	7014
0.6-0.7	3723
0.7-0.8	687
0.8-0.85	52
0.85-0.9	15
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9467	High Similarity	NPC80088
0.9467	High Similarity	NPC253561
0.9103	High Similarity	NPC119229
0.9079	High Similarity	NPC34110
0.8947	High Similarity	NPC472305
0.8889	High Similarity	NPC70685
0.8701	High Similarity	NPC7629
0.8701	High Similarity	NPC186554
0.8701	High Similarity	NPC151622
0.8701	High Similarity	NPC76966
0.869	High Similarity	NPC472983
0.8642	High Similarity	NPC297398
0.8608	High Similarity	NPC308038
0.859	High Similarity	NPC257666
0.859	High Similarity	NPC266193
0.8537	High Similarity	NPC470812
0.85	High Similarity	NPC271104
0.85	High Similarity	NPC172013
0.8481	Intermediate Similarity	NPC62336
0.8481	Intermediate Similarity	NPC207772
0.8462	Intermediate Similarity	NPC263582
0.8395	Intermediate Similarity	NPC226068
0.8375	Intermediate Similarity	NPC281138
0.8375	Intermediate Similarity	NPC152061
0.8354	Intermediate Similarity	NPC197659
0.8333	Intermediate Similarity	NPC472974
0.8313	Intermediate Similarity	NPC476412
0.8312	Intermediate Similarity	NPC35656
0.8312	Intermediate Similarity	NPC247586
0.8293	Intermediate Similarity	NPC93590
0.8276	Intermediate Similarity	NPC172101
0.8272	Intermediate Similarity	NPC138492
0.8272	Intermediate Similarity	NPC233352
0.8272	Intermediate Similarity	NPC471514
0.8272	Intermediate Similarity	NPC824
0.8272	Intermediate Similarity	NPC148685
0.8272	Intermediate Similarity	NPC104120
0.8272	Intermediate Similarity	NPC157895
0.8256	Intermediate Similarity	NPC472973
0.825	Intermediate Similarity	NPC275494
0.825	Intermediate Similarity	NPC471409
0.8193	Intermediate Similarity	NPC64600
0.8161	Intermediate Similarity	NPC134321
0.8148	Intermediate Similarity	NPC170394
0.814	Intermediate Similarity	NPC471793
0.814	Intermediate Similarity	NPC473229
0.814	Intermediate Similarity	NPC206060
0.814	Intermediate Similarity	NPC471791
0.814	Intermediate Similarity	NPC48107
0.8125	Intermediate Similarity	NPC74995
0.8125	Intermediate Similarity	NPC97377
0.8118	Intermediate Similarity	NPC472986
0.8118	Intermediate Similarity	NPC194417
0.8118	Intermediate Similarity	NPC472985
0.8118	Intermediate Similarity	NPC476043
0.8101	Intermediate Similarity	NPC476795
0.8072	Intermediate Similarity	NPC470813
0.8068	Intermediate Similarity	NPC472978
0.8068	Intermediate Similarity	NPC116726
0.8049	Intermediate Similarity	NPC476809
0.8025	Intermediate Similarity	NPC59436
0.8025	Intermediate Similarity	NPC475994
0.8025	Intermediate Similarity	NPC19443
0.8	Intermediate Similarity	NPC476426
0.8	Intermediate Similarity	NPC470525
0.8	Intermediate Similarity	NPC19907
0.8	Intermediate Similarity	NPC476245
0.7976	Intermediate Similarity	NPC169941
0.7976	Intermediate Similarity	NPC66764
0.7976	Intermediate Similarity	NPC307258
0.7976	Intermediate Similarity	NPC251475
0.7976	Intermediate Similarity	NPC110150
0.7975	Intermediate Similarity	NPC78527
0.7955	Intermediate Similarity	NPC191684
0.7955	Intermediate Similarity	NPC230332
0.7955	Intermediate Similarity	NPC128672
0.7952	Intermediate Similarity	NPC90055
0.7952	Intermediate Similarity	NPC473217
0.7949	Intermediate Similarity	NPC23954
0.7931	Intermediate Similarity	NPC474925
0.7931	Intermediate Similarity	NPC104560
0.7907	Intermediate Similarity	NPC82979
0.7907	Intermediate Similarity	NPC198761
0.7907	Intermediate Similarity	NPC179591
0.7907	Intermediate Similarity	NPC473226
0.7901	Intermediate Similarity	NPC203403
0.7901	Intermediate Similarity	NPC470428
0.7889	Intermediate Similarity	NPC472976
0.7889	Intermediate Similarity	NPC299100
0.7889	Intermediate Similarity	NPC196227
0.7889	Intermediate Similarity	NPC472977
0.7882	Intermediate Similarity	NPC40687
0.7875	Intermediate Similarity	NPC39362
0.7865	Intermediate Similarity	NPC475806
0.7865	Intermediate Similarity	NPC252433
0.7865	Intermediate Similarity	NPC472975
0.7857	Intermediate Similarity	NPC92226
0.7848	Intermediate Similarity	NPC265485
0.7848	Intermediate Similarity	NPC220939
0.7841	Intermediate Similarity	NPC118011
0.7841	Intermediate Similarity	NPC309603
0.7841	Intermediate Similarity	NPC473999
0.7841	Intermediate Similarity	NPC36668
0.7831	Intermediate Similarity	NPC469637
0.7831	Intermediate Similarity	NPC45495
0.7831	Intermediate Similarity	NPC2482
0.7816	Intermediate Similarity	NPC471792
0.7805	Intermediate Similarity	NPC297996
0.7805	Intermediate Similarity	NPC476949
0.7805	Intermediate Similarity	NPC179028
0.7805	Intermediate Similarity	NPC198240
0.7802	Intermediate Similarity	NPC259286
0.7802	Intermediate Similarity	NPC271195
0.7802	Intermediate Similarity	NPC180950
0.7791	Intermediate Similarity	NPC52628
0.7778	Intermediate Similarity	NPC109305
0.7778	Intermediate Similarity	NPC250621
0.7778	Intermediate Similarity	NPC472871
0.7778	Intermediate Similarity	NPC69454
0.7778	Intermediate Similarity	NPC151722
0.7765	Intermediate Similarity	NPC97913
0.7765	Intermediate Similarity	NPC105173
0.7765	Intermediate Similarity	NPC57370
0.7765	Intermediate Similarity	NPC49019
0.7753	Intermediate Similarity	NPC48010
0.7753	Intermediate Similarity	NPC472476
0.7753	Intermediate Similarity	NPC473099
0.775	Intermediate Similarity	NPC470299
0.7738	Intermediate Similarity	NPC121984
0.7738	Intermediate Similarity	NPC470298
0.7738	Intermediate Similarity	NPC473420
0.7738	Intermediate Similarity	NPC6663
0.7738	Intermediate Similarity	NPC116797
0.7727	Intermediate Similarity	NPC249889
0.7727	Intermediate Similarity	NPC72397
0.7727	Intermediate Similarity	NPC193843
0.7727	Intermediate Similarity	NPC472870
0.7722	Intermediate Similarity	NPC84790
0.7717	Intermediate Similarity	NPC117133
0.7717	Intermediate Similarity	NPC249954
0.7711	Intermediate Similarity	NPC283789
0.7711	Intermediate Similarity	NPC7232
0.7711	Intermediate Similarity	NPC470429
0.7711	Intermediate Similarity	NPC19900
0.7701	Intermediate Similarity	NPC94755
0.7701	Intermediate Similarity	NPC477579
0.7701	Intermediate Similarity	NPC472869
0.7701	Intermediate Similarity	NPC235341
0.7701	Intermediate Similarity	NPC95594
0.7701	Intermediate Similarity	NPC470955
0.7692	Intermediate Similarity	NPC8993
0.7692	Intermediate Similarity	NPC292793
0.7683	Intermediate Similarity	NPC61952
0.7683	Intermediate Similarity	NPC132542
0.7674	Intermediate Similarity	NPC472865
0.7674	Intermediate Similarity	NPC472326
0.7674	Intermediate Similarity	NPC30486
0.7674	Intermediate Similarity	NPC164577
0.7674	Intermediate Similarity	NPC251170
0.7674	Intermediate Similarity	NPC302360
0.7667	Intermediate Similarity	NPC233116
0.7667	Intermediate Similarity	NPC473998
0.7667	Intermediate Similarity	NPC99380
0.7667	Intermediate Similarity	NPC63748
0.7662	Intermediate Similarity	NPC263161
0.7662	Intermediate Similarity	NPC290350
0.7662	Intermediate Similarity	NPC4370
0.766	Intermediate Similarity	NPC174314
0.7654	Intermediate Similarity	NPC114236
0.7647	Intermediate Similarity	NPC103486
0.7647	Intermediate Similarity	NPC2524
0.7647	Intermediate Similarity	NPC158411
0.7647	Intermediate Similarity	NPC38796
0.764	Intermediate Similarity	NPC310236
0.764	Intermediate Similarity	NPC473100
0.764	Intermediate Similarity	NPC119416
0.764	Intermediate Similarity	NPC184663
0.764	Intermediate Similarity	NPC472970
0.764	Intermediate Similarity	NPC5509
0.764	Intermediate Similarity	NPC472971
0.7634	Intermediate Similarity	NPC170131
0.7629	Intermediate Similarity	NPC1679
0.7625	Intermediate Similarity	NPC186042
0.7619	Intermediate Similarity	NPC306095
0.7619	Intermediate Similarity	NPC287817
0.7619	Intermediate Similarity	NPC74445
0.7619	Intermediate Similarity	NPC472478
0.7619	Intermediate Similarity	NPC108955
0.7614	Intermediate Similarity	NPC476409
0.7609	Intermediate Similarity	NPC183012
0.7609	Intermediate Similarity	NPC316215
0.76	Intermediate Similarity	NPC174956
0.759	Intermediate Similarity	NPC178852
0.759	Intermediate Similarity	NPC321514
0.759	Intermediate Similarity	NPC239098
0.759	Intermediate Similarity	NPC189485
0.759	Intermediate Similarity	NPC74410
0.7586	Intermediate Similarity	NPC474853
0.7586	Intermediate Similarity	NPC109528
0.7586	Intermediate Similarity	NPC471224

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 NPC472301 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1557
0.2-0.3	3810
0.3-0.4	2484
0.4-0.5	731
0.5-0.6	234
0.6-0.7	164
0.7-0.8	16
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7701	Intermediate Similarity	NPD4519	Discontinued
0.7701	Intermediate Similarity	NPD3618	Phase 1
0.7701	Intermediate Similarity	NPD4623	Approved
0.75	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD6079	Approved
0.7471	Intermediate Similarity	NPD3665	Phase 1
0.7471	Intermediate Similarity	NPD3133	Approved
0.7471	Intermediate Similarity	NPD3666	Approved
0.7444	Intermediate Similarity	NPD5328	Approved
0.7442	Intermediate Similarity	NPD4221	Approved
0.7442	Intermediate Similarity	NPD4223	Phase 3
0.7412	Intermediate Similarity	NPD4695	Discontinued
0.7391	Intermediate Similarity	NPD4202	Approved
0.734	Intermediate Similarity	NPD4697	Phase 3
0.732	Intermediate Similarity	NPD5211	Phase 2
0.7303	Intermediate Similarity	NPD5690	Phase 2
0.7283	Intermediate Similarity	NPD7515	Phase 2
0.7273	Intermediate Similarity	NPD4197	Approved
0.7253	Intermediate Similarity	NPD4753	Phase 2
0.7241	Intermediate Similarity	NPD3667	Approved
0.7191	Intermediate Similarity	NPD1694	Approved
0.7191	Intermediate Similarity	NPD5329	Approved
0.7191	Intermediate Similarity	NPD1696	Phase 3
0.7172	Intermediate Similarity	NPD5141	Approved
0.7158	Intermediate Similarity	NPD5221	Approved
0.7158	Intermediate Similarity	NPD5222	Approved
0.7158	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7748	Approved
0.7113	Intermediate Similarity	NPD5285	Approved
0.7113	Intermediate Similarity	NPD4696	Approved
0.7113	Intermediate Similarity	NPD5286	Approved
0.7111	Intermediate Similarity	NPD4138	Approved
0.7111	Intermediate Similarity	NPD4690	Approved
0.7111	Intermediate Similarity	NPD5205	Approved
0.7111	Intermediate Similarity	NPD5279	Phase 3
0.7111	Intermediate Similarity	NPD4688	Approved
0.7111	Intermediate Similarity	NPD4689	Approved
0.7111	Intermediate Similarity	NPD4694	Approved
0.7111	Intermediate Similarity	NPD5280	Approved
0.7111	Intermediate Similarity	NPD4693	Phase 3
0.7089	Intermediate Similarity	NPD7331	Phase 2
0.7083	Intermediate Similarity	NPD4755	Approved
0.7083	Intermediate Similarity	NPD5173	Approved
0.7079	Intermediate Similarity	NPD4786	Approved
0.7053	Intermediate Similarity	NPD4629	Approved
0.7053	Intermediate Similarity	NPD5210	Approved
0.7045	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5223	Approved
0.7033	Intermediate Similarity	NPD3573	Approved
0.7013	Intermediate Similarity	NPD368	Approved
0.6977	Remote Similarity	NPD3617	Approved
0.697	Remote Similarity	NPD5225	Approved
0.697	Remote Similarity	NPD4633	Approved
0.697	Remote Similarity	NPD5226	Approved
0.697	Remote Similarity	NPD5224	Approved
0.6962	Remote Similarity	NPD7341	Phase 2
0.6939	Remote Similarity	NPD4700	Approved
0.6907	Remote Similarity	NPD7902	Approved
0.69	Remote Similarity	NPD5175	Approved
0.69	Remote Similarity	NPD5174	Approved
0.6897	Remote Similarity	NPD4195	Approved
0.6875	Remote Similarity	NPD5695	Phase 3
0.6778	Remote Similarity	NPD4788	Approved
0.6768	Remote Similarity	NPD7640	Approved
0.6768	Remote Similarity	NPD7639	Approved
0.6747	Remote Similarity	NPD4691	Approved
0.6739	Remote Similarity	NPD5330	Approved
0.6739	Remote Similarity	NPD6684	Approved
0.6739	Remote Similarity	NPD7146	Approved
0.6739	Remote Similarity	NPD6409	Approved
0.6739	Remote Similarity	NPD7334	Approved
0.6739	Remote Similarity	NPD7521	Approved
0.6737	Remote Similarity	NPD5284	Approved
0.6737	Remote Similarity	NPD5281	Approved
0.6735	Remote Similarity	NPD6083	Phase 2
0.6735	Remote Similarity	NPD6084	Phase 2
0.6733	Remote Similarity	NPD4754	Approved
0.6703	Remote Similarity	NPD3668	Phase 3
0.6699	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD342	Phase 1
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD5696	Approved
0.6635	Remote Similarity	NPD6881	Approved
0.6635	Remote Similarity	NPD4730	Approved
0.6635	Remote Similarity	NPD5128	Approved
0.6635	Remote Similarity	NPD6899	Approved
0.6635	Remote Similarity	NPD6011	Approved
0.6635	Remote Similarity	NPD4729	Approved
0.6632	Remote Similarity	NPD4096	Approved
0.6627	Remote Similarity	NPD4137	Phase 3
0.6606	Remote Similarity	NPD7115	Discovery
0.6602	Remote Similarity	NPD5739	Approved
0.6602	Remote Similarity	NPD4768	Approved
0.6602	Remote Similarity	NPD6675	Approved
0.6602	Remote Similarity	NPD7128	Approved
0.6602	Remote Similarity	NPD6402	Approved
0.6602	Remote Similarity	NPD4767	Approved
0.66	Remote Similarity	NPD6404	Discontinued
0.6598	Remote Similarity	NPD7900	Approved
0.6598	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6672	Approved
0.6596	Remote Similarity	NPD6903	Approved
0.6596	Remote Similarity	NPD5737	Approved
0.6596	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6013	Approved
0.6571	Remote Similarity	NPD6012	Approved
0.6571	Remote Similarity	NPD6014	Approved
0.6556	Remote Similarity	NPD4692	Approved
0.6556	Remote Similarity	NPD4139	Approved
0.6548	Remote Similarity	NPD4747	Approved
0.6538	Remote Similarity	NPD5701	Approved
0.6531	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7645	Phase 2
0.6512	Remote Similarity	NPD4058	Approved
0.6509	Remote Similarity	NPD5249	Phase 3
0.6509	Remote Similarity	NPD6883	Approved
0.6509	Remote Similarity	NPD7290	Approved
0.6509	Remote Similarity	NPD5247	Approved
0.6509	Remote Similarity	NPD5248	Approved
0.6509	Remote Similarity	NPD5250	Approved
0.6509	Remote Similarity	NPD5169	Approved
0.6509	Remote Similarity	NPD4634	Approved
0.6509	Remote Similarity	NPD7102	Approved
0.6509	Remote Similarity	NPD5251	Approved
0.6509	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5135	Approved
0.6495	Remote Similarity	NPD6399	Phase 3
0.6495	Remote Similarity	NPD5133	Approved
0.6476	Remote Similarity	NPD7320	Approved
0.6476	Remote Similarity	NPD5168	Approved
0.6452	Remote Similarity	NPD5363	Approved
0.6452	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6649	Approved
0.6449	Remote Similarity	NPD6617	Approved
0.6449	Remote Similarity	NPD6650	Approved
0.6449	Remote Similarity	NPD6869	Approved
0.6449	Remote Similarity	NPD5216	Approved
0.6449	Remote Similarity	NPD5215	Approved
0.6449	Remote Similarity	NPD5127	Approved
0.6449	Remote Similarity	NPD8130	Phase 1
0.6449	Remote Similarity	NPD6847	Approved
0.6449	Remote Similarity	NPD5217	Approved
0.6444	Remote Similarity	NPD7525	Registered
0.6437	Remote Similarity	NPD8264	Approved
0.6429	Remote Similarity	NPD6001	Approved
0.6421	Remote Similarity	NPD4518	Approved
0.6421	Remote Similarity	NPD5208	Approved
0.6415	Remote Similarity	NPD6373	Approved
0.6415	Remote Similarity	NPD6372	Approved
0.6392	Remote Similarity	NPD5693	Phase 1
0.6389	Remote Similarity	NPD8297	Approved
0.6389	Remote Similarity	NPD6882	Approved
0.6364	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6101	Approved
0.6354	Remote Similarity	NPD6673	Approved
0.6354	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6080	Approved
0.6354	Remote Similarity	NPD6904	Approved
0.633	Remote Similarity	NPD4632	Approved
0.6322	Remote Similarity	NPD5733	Approved
0.6322	Remote Similarity	NPD4687	Approved
0.6316	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD5091	Approved
0.63	Remote Similarity	NPD7614	Phase 1
0.6296	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD4756	Discovery
0.6289	Remote Similarity	NPD5692	Phase 3
0.6289	Remote Similarity	NPD5207	Approved
0.6279	Remote Similarity	NPD5276	Approved
0.6279	Remote Similarity	NPD4243	Approved
0.6273	Remote Similarity	NPD5167	Approved
0.6264	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7339	Approved
0.625	Remote Similarity	NPD6942	Approved
0.6237	Remote Similarity	NPD5362	Discontinued
0.6224	Remote Similarity	NPD6050	Approved
0.6224	Remote Similarity	NPD5694	Approved
0.6224	Remote Similarity	NPD6411	Approved
0.6222	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6274	Approved
0.6211	Remote Similarity	NPD6098	Approved
0.6204	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD287	Approved
0.6176	Remote Similarity	NPD5290	Discontinued
0.6168	Remote Similarity	NPD6686	Approved
0.6161	Remote Similarity	NPD6317	Approved
0.6161	Remote Similarity	NPD6009	Approved
0.6154	Remote Similarity	NPD7632	Discontinued
0.6147	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD6924	Approved
0.6136	Remote Similarity	NPD4785	Approved
0.6136	Remote Similarity	NPD6926	Approved
0.6136	Remote Similarity	NPD4784	Approved
0.6132	Remote Similarity	NPD6008	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