NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.16
Volume:	269.345
LogP:	1.434
LogD:	0.736
LogS:	-2.517
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.748
Synthetic Accessibility Score:	4.604
Fsp3:	0.667
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:	-4.606
MDCK Permeability:	1.838838215917349e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.883
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.862
Plasma Protein Binding (PPB):	62.65963363647461%
Volume Distribution (VD):	0.921
Pgp-substrate:	40.39901351928711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.867
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.335
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.189
CYP3A4-inhibitor:	0.04
CYP3A4-substrate:	0.64

ADMET: Excretion

Clearance (CL):	6.971
Half-life (T1/2):	0.927

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.145
Drug-inuced Liver Injury (DILI):	0.058
AMES Toxicity:	0.228
Rat Oral Acute Toxicity:	0.97
Maximum Recommended Daily Dose:	0.902
Skin Sensitization:	0.447
Carcinogencity:	0.881
Eye Corrosion:	0.005
Eye Irritation:	0.087
Respiratory Toxicity:	0.684

Download Data

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

Natural Product: NPC15807

Natural Product ID:	NPC15807
*Common Name:**	4,6-Diene-1Beta,15-Dihydroxyeudesma-3-One
IUPAC Name:	(4R,4aR)-4-hydroxy-1-(hydroxymethyl)-4a-methyl-7-propan-2-yl-3,4,5,6-tetrahydronaphthalen-2-one
Synonyms:
Standard InCHIKey:	ARYHWGXGRJYLNK-HUUCEWRRSA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-9(2)10-4-5-15(3)12(6-10)11(8-16)13(17)7-14(15)18/h6,9,14,16,18H,4-5,7-8H2,1-3H3/t14-,15-/m1/s1
SMILES:	OCC1=C2C=C(CC[C@]2([C@@H](CC1=O)O)C)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651035
PubChem CID:	50901153
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0000101] Eudesmane, isoeudesmane or cycloeudesmane 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
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	stem	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	twig	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[20939540]
NPO8087	Aglaia foveolata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22817615]
NPO8087	Aglaia foveolata	Species	Meliaceae	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
ED50	1
IC50	1

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	10.0	uM	PMID[448522]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC50	>	20000.0	nM	PMID[448522]

☑ 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 NPC15807 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	182
0.1-0.2	1064
0.2-0.3	4819
0.3-0.4	11204
0.4-0.5	14263
0.5-0.6	7586
0.6-0.7	3143
0.7-0.8	401
0.8-0.85	25
0.85-0.9	9
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8642	High Similarity	NPC178852
0.8554	High Similarity	NPC470298
0.8537	High Similarity	NPC281138
0.8452	Intermediate Similarity	NPC158411
0.8452	Intermediate Similarity	NPC38796
0.8315	Intermediate Similarity	NPC473099
0.8313	Intermediate Similarity	NPC308038
0.8276	Intermediate Similarity	NPC472985
0.8276	Intermediate Similarity	NPC472986
0.8235	Intermediate Similarity	NPC93590
0.8222	Intermediate Similarity	NPC116726
0.8222	Intermediate Similarity	NPC73457
0.8214	Intermediate Similarity	NPC148685
0.8214	Intermediate Similarity	NPC172013
0.8214	Intermediate Similarity	NPC157895
0.8214	Intermediate Similarity	NPC104120
0.8202	Intermediate Similarity	NPC473100
0.8193	Intermediate Similarity	NPC475994
0.8172	Intermediate Similarity	NPC471916
0.8161	Intermediate Similarity	NPC179006
0.8161	Intermediate Similarity	NPC474853
0.8118	Intermediate Similarity	NPC6663
0.8095	Intermediate Similarity	NPC19900
0.8072	Intermediate Similarity	NPC471061
0.8072	Intermediate Similarity	NPC197659
0.8068	Intermediate Similarity	NPC194417
0.8068	Intermediate Similarity	NPC472974
0.8043	Intermediate Similarity	NPC196227
0.8022	Intermediate Similarity	NPC233116
0.7978	Intermediate Similarity	NPC287079
0.7955	Intermediate Similarity	NPC187529
0.7952	Intermediate Similarity	NPC263582
0.7952	Intermediate Similarity	NPC470525
0.7931	Intermediate Similarity	NPC169941
0.7931	Intermediate Similarity	NPC251475
0.7917	Intermediate Similarity	NPC207885
0.7907	Intermediate Similarity	NPC116797
0.7907	Intermediate Similarity	NPC121984
0.7901	Intermediate Similarity	NPC84790
0.7895	Intermediate Similarity	NPC103051
0.7882	Intermediate Similarity	NPC246458
0.7872	Intermediate Similarity	NPC94337
0.7865	Intermediate Similarity	NPC470955
0.7857	Intermediate Similarity	NPC257666
0.7857	Intermediate Similarity	NPC86917
0.7857	Intermediate Similarity	NPC74995
0.7857	Intermediate Similarity	NPC266193
0.7857	Intermediate Similarity	NPC203403
0.7849	Intermediate Similarity	NPC78159
0.7849	Intermediate Similarity	NPC474690
0.7841	Intermediate Similarity	NPC40687
0.7805	Intermediate Similarity	NPC186042
0.7802	Intermediate Similarity	NPC472983
0.7802	Intermediate Similarity	NPC309603
0.7802	Intermediate Similarity	NPC473999
0.7802	Intermediate Similarity	NPC36668
0.7802	Intermediate Similarity	NPC472971
0.7802	Intermediate Similarity	NPC472970
0.7802	Intermediate Similarity	NPC118011
0.7791	Intermediate Similarity	NPC45495
0.7791	Intermediate Similarity	NPC271104
0.7791	Intermediate Similarity	NPC74086
0.7791	Intermediate Similarity	NPC471514
0.7789	Intermediate Similarity	NPC320306
0.7789	Intermediate Similarity	NPC161147
0.7778	Intermediate Similarity	NPC272039
0.7778	Intermediate Similarity	NPC298904
0.7778	Intermediate Similarity	NPC220930
0.7778	Intermediate Similarity	NPC173321
0.7766	Intermediate Similarity	NPC271195
0.7766	Intermediate Similarity	NPC476245
0.7765	Intermediate Similarity	NPC478122
0.7765	Intermediate Similarity	NPC62336
0.7755	Intermediate Similarity	NPC95899
0.7755	Intermediate Similarity	NPC131366
0.7753	Intermediate Similarity	NPC476426
0.7753	Intermediate Similarity	NPC32037
0.7742	Intermediate Similarity	NPC109305
0.7742	Intermediate Similarity	NPC69454
0.7742	Intermediate Similarity	NPC134826
0.7738	Intermediate Similarity	NPC250621
0.7738	Intermediate Similarity	NPC472305
0.7732	Intermediate Similarity	NPC112613
0.7727	Intermediate Similarity	NPC66764
0.7727	Intermediate Similarity	NPC64600
0.7727	Intermediate Similarity	NPC110150
0.7727	Intermediate Similarity	NPC105173
0.7717	Intermediate Similarity	NPC48010
0.7717	Intermediate Similarity	NPC134321
0.7717	Intermediate Similarity	NPC69622
0.7711	Intermediate Similarity	NPC215050
0.7701	Intermediate Similarity	NPC14151
0.77	Intermediate Similarity	NPC472925
0.7692	Intermediate Similarity	NPC474854
0.7692	Intermediate Similarity	NPC72397
0.7692	Intermediate Similarity	NPC471722
0.7692	Intermediate Similarity	NPC53454
0.7684	Intermediate Similarity	NPC117133
0.7674	Intermediate Similarity	NPC152061
0.7674	Intermediate Similarity	NPC7232
0.7667	Intermediate Similarity	NPC198761
0.7667	Intermediate Similarity	NPC473226
0.7667	Intermediate Similarity	NPC222613
0.7667	Intermediate Similarity	NPC118648
0.7667	Intermediate Similarity	NPC239685
0.7667	Intermediate Similarity	NPC475022
0.766	Intermediate Similarity	NPC299100
0.766	Intermediate Similarity	NPC181393
0.766	Intermediate Similarity	NPC474882
0.766	Intermediate Similarity	NPC217624
0.764	Intermediate Similarity	NPC472326
0.7634	Intermediate Similarity	NPC63748
0.7634	Intermediate Similarity	NPC475806
0.7634	Intermediate Similarity	NPC142838
0.7634	Intermediate Similarity	NPC473998
0.7629	Intermediate Similarity	NPC327431
0.7625	Intermediate Similarity	NPC96962
0.7619	Intermediate Similarity	NPC114236
0.7609	Intermediate Similarity	NPC472489
0.7609	Intermediate Similarity	NPC472676
0.7609	Intermediate Similarity	NPC186688
0.7609	Intermediate Similarity	NPC472973
0.7609	Intermediate Similarity	NPC472688
0.7604	Intermediate Similarity	NPC474785
0.7604	Intermediate Similarity	NPC474938
0.759	Intermediate Similarity	NPC275098
0.759	Intermediate Similarity	NPC247586
0.7586	Intermediate Similarity	NPC2482
0.7582	Intermediate Similarity	NPC136548
0.7582	Intermediate Similarity	NPC141292
0.7579	Intermediate Similarity	NPC127063
0.7579	Intermediate Similarity	NPC180950
0.7579	Intermediate Similarity	NPC259286
0.7579	Intermediate Similarity	NPC280725
0.7576	Intermediate Similarity	NPC475050
0.7576	Intermediate Similarity	NPC473624
0.7558	Intermediate Similarity	NPC207772
0.7558	Intermediate Similarity	NPC189485
0.7556	Intermediate Similarity	NPC474083
0.7556	Intermediate Similarity	NPC70685
0.7553	Intermediate Similarity	NPC472942
0.7551	Intermediate Similarity	NPC282524
0.7551	Intermediate Similarity	NPC472924
0.7551	Intermediate Similarity	NPC470184
0.7551	Intermediate Similarity	NPC472637
0.7529	Intermediate Similarity	NPC151622
0.7529	Intermediate Similarity	NPC7629
0.7528	Intermediate Similarity	NPC297398
0.7527	Intermediate Similarity	NPC128672
0.7527	Intermediate Similarity	NPC230332
0.7526	Intermediate Similarity	NPC235464
0.7526	Intermediate Similarity	NPC478056
0.7526	Intermediate Similarity	NPC166745
0.7526	Intermediate Similarity	NPC471717
0.75	Intermediate Similarity	NPC471724
0.75	Intermediate Similarity	NPC292491
0.75	Intermediate Similarity	NPC476796
0.75	Intermediate Similarity	NPC250757
0.75	Intermediate Similarity	NPC202833
0.75	Intermediate Similarity	NPC301534
0.75	Intermediate Similarity	NPC136150
0.75	Intermediate Similarity	NPC473420
0.75	Intermediate Similarity	NPC310752
0.75	Intermediate Similarity	NPC213223
0.75	Intermediate Similarity	NPC471793
0.75	Intermediate Similarity	NPC249954
0.75	Intermediate Similarity	NPC471791
0.7476	Intermediate Similarity	NPC286880
0.7475	Intermediate Similarity	NPC234892
0.7475	Intermediate Similarity	NPC293753
0.7475	Intermediate Similarity	NPC273005
0.7475	Intermediate Similarity	NPC469606
0.7475	Intermediate Similarity	NPC31058
0.7474	Intermediate Similarity	NPC472976
0.7474	Intermediate Similarity	NPC245972
0.7474	Intermediate Similarity	NPC474328
0.7474	Intermediate Similarity	NPC53685
0.7474	Intermediate Similarity	NPC469406
0.7474	Intermediate Similarity	NPC196485
0.7474	Intermediate Similarity	NPC473162
0.7474	Intermediate Similarity	NPC472977
0.7474	Intermediate Similarity	NPC8993
0.7473	Intermediate Similarity	NPC82979
0.7473	Intermediate Similarity	NPC474778
0.7473	Intermediate Similarity	NPC145879
0.7473	Intermediate Similarity	NPC476043
0.7473	Intermediate Similarity	NPC94666
0.7473	Intermediate Similarity	NPC31564
0.7473	Intermediate Similarity	NPC474733
0.7473	Intermediate Similarity	NPC72133
0.7473	Intermediate Similarity	NPC474732
0.7451	Intermediate Similarity	NPC322903
0.7449	Intermediate Similarity	NPC266955
0.7449	Intermediate Similarity	NPC154072
0.7447	Intermediate Similarity	NPC472978
0.7447	Intermediate Similarity	NPC131872
0.7447	Intermediate Similarity	NPC172101
0.7444	Intermediate Similarity	NPC7927
0.7444	Intermediate Similarity	NPC476412
0.7444	Intermediate Similarity	NPC230527

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 NPC15807 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1526
0.2-0.3	3791
0.3-0.4	2422
0.4-0.5	835
0.5-0.6	309
0.6-0.7	85
0.7-0.8	8
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
0.7791	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD5779	Approved
0.7742	Intermediate Similarity	NPD5778	Approved
0.7556	Intermediate Similarity	NPD1696	Phase 3
0.7473	Intermediate Similarity	NPD3618	Phase 1
0.7473	Intermediate Similarity	NPD5279	Phase 3
0.7416	Intermediate Similarity	NPD3667	Approved
0.7412	Intermediate Similarity	NPD8264	Approved
0.7263	Intermediate Similarity	NPD6411	Approved
0.7253	Intermediate Similarity	NPD3133	Approved
0.7253	Intermediate Similarity	NPD3665	Phase 1
0.7253	Intermediate Similarity	NPD3666	Approved
0.7253	Intermediate Similarity	NPD4786	Approved
0.7234	Intermediate Similarity	NPD5328	Approved
0.7083	Intermediate Similarity	NPD6079	Approved
0.7083	Intermediate Similarity	NPD7515	Phase 2
0.7053	Intermediate Similarity	NPD6101	Approved
0.7053	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4202	Approved
0.6915	Remote Similarity	NPD4519	Discontinued
0.6915	Remote Similarity	NPD4694	Approved
0.6915	Remote Similarity	NPD4623	Approved
0.6915	Remote Similarity	NPD5280	Approved
0.6907	Remote Similarity	NPD7637	Suspended
0.6813	Remote Similarity	NPD4695	Discontinued
0.6809	Remote Similarity	NPD5363	Approved
0.6804	Remote Similarity	NPD5785	Approved
0.68	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5222	Approved
0.68	Remote Similarity	NPD5221	Approved
0.68	Remote Similarity	NPD4697	Phase 3
0.6796	Remote Similarity	NPD5211	Phase 2
0.6771	Remote Similarity	NPD4518	Approved
0.6768	Remote Similarity	NPD7748	Approved
0.6765	Remote Similarity	NPD7640	Approved
0.6765	Remote Similarity	NPD7639	Approved
0.6737	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7983	Approved
0.6733	Remote Similarity	NPD5173	Approved
0.6733	Remote Similarity	NPD4755	Approved
0.6703	Remote Similarity	NPD6929	Approved
0.6702	Remote Similarity	NPD3668	Phase 3
0.6701	Remote Similarity	NPD4753	Phase 2
0.6701	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5776	Phase 2
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD7331	Phase 2
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD4269	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD6925	Approved
0.6634	Remote Similarity	NPD7839	Suspended
0.6632	Remote Similarity	NPD1694	Approved
0.663	Remote Similarity	NPD7514	Phase 3
0.663	Remote Similarity	NPD6930	Phase 2
0.663	Remote Similarity	NPD7332	Phase 2
0.663	Remote Similarity	NPD6931	Approved
0.6607	Remote Similarity	NPD7115	Discovery
0.6602	Remote Similarity	NPD5285	Approved
0.6602	Remote Similarity	NPD5286	Approved
0.6602	Remote Similarity	NPD4700	Approved
0.6602	Remote Similarity	NPD4696	Approved
0.66	Remote Similarity	NPD5282	Discontinued
0.6593	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7145	Approved
0.6569	Remote Similarity	NPD7902	Approved
0.6566	Remote Similarity	NPD5284	Approved
0.6566	Remote Similarity	NPD5281	Approved
0.6562	Remote Similarity	NPD5690	Phase 2
0.6559	Remote Similarity	NPD6902	Approved
0.6538	Remote Similarity	NPD5223	Approved
0.6526	Remote Similarity	NPD4197	Approved
0.6517	Remote Similarity	NPD5733	Approved
0.6517	Remote Similarity	NPD4687	Approved
0.65	Remote Similarity	NPD6399	Phase 3
0.6495	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4756	Discovery
0.6477	Remote Similarity	NPD5276	Approved
0.6476	Remote Similarity	NPD4633	Approved
0.6476	Remote Similarity	NPD5225	Approved
0.6476	Remote Similarity	NPD5224	Approved
0.6476	Remote Similarity	NPD5226	Approved
0.6465	Remote Similarity	NPD46	Approved
0.6465	Remote Similarity	NPD6698	Approved
0.6465	Remote Similarity	NPD4096	Approved
0.6458	Remote Similarity	NPD5329	Approved
0.6452	Remote Similarity	NPD4252	Approved
0.6444	Remote Similarity	NPD8039	Approved
0.6421	Remote Similarity	NPD6695	Phase 3
0.6415	Remote Similarity	NPD5175	Approved
0.6415	Remote Similarity	NPD4754	Approved
0.6415	Remote Similarity	NPD5174	Approved
0.6413	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD3617	Approved
0.6392	Remote Similarity	NPD4690	Approved
0.6392	Remote Similarity	NPD4138	Approved
0.6392	Remote Similarity	NPD4688	Approved
0.6392	Remote Similarity	NPD7521	Approved
0.6392	Remote Similarity	NPD5205	Approved
0.6392	Remote Similarity	NPD4693	Phase 3
0.6392	Remote Similarity	NPD5786	Approved
0.6392	Remote Similarity	NPD4689	Approved
0.6392	Remote Similarity	NPD7146	Approved
0.6392	Remote Similarity	NPD7334	Approved
0.6392	Remote Similarity	NPD5330	Approved
0.6392	Remote Similarity	NPD6409	Approved
0.6392	Remote Similarity	NPD6684	Approved
0.6386	Remote Similarity	NPD368	Approved
0.6383	Remote Similarity	NPD6898	Phase 1
0.6374	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD4629	Approved
0.6373	Remote Similarity	NPD5210	Approved
0.6373	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5695	Phase 3
0.6354	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD7341	Phase 2
0.6337	Remote Similarity	NPD5133	Approved
0.6333	Remote Similarity	NPD6924	Approved
0.6333	Remote Similarity	NPD4058	Approved
0.6333	Remote Similarity	NPD6926	Approved
0.6304	Remote Similarity	NPD6932	Approved
0.6296	Remote Similarity	NPD6675	Approved
0.6296	Remote Similarity	NPD4767	Approved
0.6296	Remote Similarity	NPD7128	Approved
0.6296	Remote Similarity	NPD6402	Approved
0.6296	Remote Similarity	NPD5739	Approved
0.6296	Remote Similarity	NPD4768	Approved
0.6292	Remote Similarity	NPD7151	Approved
0.6292	Remote Similarity	NPD7152	Approved
0.6292	Remote Similarity	NPD7150	Approved
0.6289	Remote Similarity	NPD6893	Approved
0.6286	Remote Similarity	NPD6404	Discontinued
0.6275	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7900	Approved
0.6264	Remote Similarity	NPD6942	Approved
0.6264	Remote Similarity	NPD7339	Approved
0.6263	Remote Similarity	NPD6903	Approved
0.6263	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6110	Phase 1
0.625	Remote Similarity	NPD6922	Approved
0.625	Remote Similarity	NPD6923	Approved
0.625	Remote Similarity	NPD6083	Phase 2
0.625	Remote Similarity	NPD342	Phase 1
0.625	Remote Similarity	NPD7154	Phase 3
0.625	Remote Similarity	NPD5362	Discontinued
0.625	Remote Similarity	NPD4137	Phase 3
0.625	Remote Similarity	NPD6084	Phase 2
0.6239	Remote Similarity	NPD6412	Phase 2
0.6239	Remote Similarity	NPD5701	Approved
0.6239	Remote Similarity	NPD5697	Approved
0.6222	Remote Similarity	NPD4732	Discontinued
0.6216	Remote Similarity	NPD6371	Approved
0.6211	Remote Similarity	NPD5369	Approved
0.6196	Remote Similarity	NPD6933	Approved
0.6195	Remote Similarity	NPD4632	Approved
0.619	Remote Similarity	NPD4193	Approved
0.619	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4194	Approved
0.619	Remote Similarity	NPD4192	Approved
0.619	Remote Similarity	NPD4191	Approved
0.6186	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD4730	Approved
0.6182	Remote Similarity	NPD6011	Approved
0.6182	Remote Similarity	NPD6899	Approved
0.6182	Remote Similarity	NPD5168	Approved
0.6182	Remote Similarity	NPD4729	Approved
0.6182	Remote Similarity	NPD5128	Approved
0.6182	Remote Similarity	NPD6881	Approved
0.6182	Remote Similarity	NPD7320	Approved
0.618	Remote Similarity	NPD4691	Approved
0.618	Remote Similarity	NPD7144	Approved
0.618	Remote Similarity	NPD4747	Approved
0.618	Remote Similarity	NPD7143	Approved
0.6173	Remote Similarity	NPD4219	Approved
0.617	Remote Similarity	NPD6683	Phase 2
0.617	Remote Similarity	NPD7645	Phase 2
0.6168	Remote Similarity	NPD7632	Discontinued
0.6162	Remote Similarity	NPD7524	Approved
0.6162	Remote Similarity	NPD7750	Discontinued
0.6162	Remote Similarity	NPD3573	Approved
0.6154	Remote Similarity	NPD6054	Approved
0.6154	Remote Similarity	NPD6319	Approved
0.6154	Remote Similarity	NPD6059	Approved
0.6147	Remote Similarity	NPD7333	Discontinued
0.6147	Remote Similarity	NPD6008	Approved
0.6146	Remote Similarity	NPD5209	Approved
0.6146	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5692	Phase 3
0.6139	Remote Similarity	NPD5207	Approved
0.6126	Remote Similarity	NPD6373	Approved
0.6126	Remote Similarity	NPD6014	Approved
0.6126	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6372	Approved
0.6126	Remote Similarity	NPD6013	Approved
0.6126	Remote Similarity	NPD6012	Approved
0.6122	Remote Similarity	NPD7520	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