NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	236.18
Volume:	269.111
LogP:	3.103
LogD:	3.025
LogS:	-3.718
# Rotatable Bonds:	0
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.518
Synthetic Accessibility Score:	4.6
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.524
MDCK Permeability:	2.6680279916035943e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.038
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.227
Plasma Protein Binding (PPB):	82.1407241821289%
Volume Distribution (VD):	0.786
Pgp-substrate:	4.78488302230835%

ADMET: Metabolism

CYP1A2-inhibitor:	0.132
CYP1A2-substrate:	0.495
CYP2C19-inhibitor:	0.167
CYP2C19-substrate:	0.418
CYP2C9-inhibitor:	0.184
CYP2C9-substrate:	0.779
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.735
CYP3A4-inhibitor:	0.036
CYP3A4-substrate:	0.312

ADMET: Excretion

Clearance (CL):	4.006
Half-life (T1/2):	0.334

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.165
Drug-inuced Liver Injury (DILI):	0.156
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.91
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.794
Carcinogencity:	0.056
Eye Corrosion:	0.014
Eye Irritation:	0.494
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC250928

Natural Product ID:	NPC250928
*Common Name:**	Litseahumulanes A
IUPAC Name:	(4R,5E,8R)-8-hydroxy-4,7,7-trimethyl-11-methylidenecycloundec-5-en-1-one
Synonyms:
Standard InCHIKey:	SSWUIXHLQYARRL-YCNBAEJOSA-N
Standard InCHI:	InChI=1S/C15H24O2/c1-11-5-7-13(16)12(2)6-8-14(17)15(3,4)10-9-11/h9-11,14,17H,2,5-8H2,1,3-4H3/b10-9+/t11-,14-/m1/s1
SMILES:	C[C@@H]1CCC(=O)C(=C)CC[C@H](C(/C=C/1)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505858
PubChem CID:	11118053
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
NPO22051	Litsea verticillata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762792]
NPO22051	Litsea verticillata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22051	Litsea verticillata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22051	Litsea verticillata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22051	Litsea verticillata	Species	Lauraceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	=	39.0	%	PMID[548411]

☑ 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 NPC250928 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	172
0.1-0.2	1365
0.2-0.3	7101
0.3-0.4	16044
0.4-0.5	9256
0.5-0.6	6233
0.6-0.7	2300
0.7-0.8	200
0.8-0.85	15
0.85-0.9	9
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC10758
0.875	High Similarity	NPC276769
0.8472	Intermediate Similarity	NPC474011
0.8356	Intermediate Similarity	NPC469646
0.8243	Intermediate Similarity	NPC211279
0.8235	Intermediate Similarity	NPC474329
0.8235	Intermediate Similarity	NPC474304
0.8133	Intermediate Similarity	NPC475994
0.8116	Intermediate Similarity	NPC197089
0.8108	Intermediate Similarity	NPC470525
0.806	Intermediate Similarity	NPC260573
0.8026	Intermediate Similarity	NPC136033
0.8026	Intermediate Similarity	NPC181195
0.8026	Intermediate Similarity	NPC261125
0.7973	Intermediate Similarity	NPC472256
0.7973	Intermediate Similarity	NPC114236
0.7945	Intermediate Similarity	NPC275098
0.7895	Intermediate Similarity	NPC62336
0.7895	Intermediate Similarity	NPC321180
0.7792	Intermediate Similarity	NPC19900
0.7778	Intermediate Similarity	NPC469914
0.7763	Intermediate Similarity	NPC86917
0.7763	Intermediate Similarity	NPC197659
0.775	Intermediate Similarity	NPC7927
0.775	Intermediate Similarity	NPC230527
0.7746	Intermediate Similarity	NPC96962
0.7733	Intermediate Similarity	NPC216791
0.7722	Intermediate Similarity	NPC38796
0.7722	Intermediate Similarity	NPC158411
0.7722	Intermediate Similarity	NPC279186
0.7703	Intermediate Similarity	NPC186042
0.7683	Intermediate Similarity	NPC472324
0.7671	Intermediate Similarity	NPC173321
0.7671	Intermediate Similarity	NPC318766
0.7662	Intermediate Similarity	NPC474056
0.7662	Intermediate Similarity	NPC178852
0.7654	Intermediate Similarity	NPC476426
0.7654	Intermediate Similarity	NPC36350
0.7632	Intermediate Similarity	NPC263582
0.7625	Intermediate Similarity	NPC476082
0.7625	Intermediate Similarity	NPC278648
0.7625	Intermediate Similarity	NPC64600
0.76	Intermediate Similarity	NPC215050
0.7595	Intermediate Similarity	NPC14151
0.7595	Intermediate Similarity	NPC136150
0.759	Intermediate Similarity	NPC158778
0.7564	Intermediate Similarity	NPC281138
0.7564	Intermediate Similarity	NPC7232
0.7564	Intermediate Similarity	NPC308038
0.7561	Intermediate Similarity	NPC183736
0.7532	Intermediate Similarity	NPC74995
0.7532	Intermediate Similarity	NPC471061
0.7532	Intermediate Similarity	NPC476007
0.7531	Intermediate Similarity	NPC470812
0.75	Intermediate Similarity	NPC474885
0.747	Intermediate Similarity	NPC298904
0.7468	Intermediate Similarity	NPC45495
0.7468	Intermediate Similarity	NPC470946
0.7468	Intermediate Similarity	NPC172013
0.7468	Intermediate Similarity	NPC470947
0.7468	Intermediate Similarity	NPC2482
0.7468	Intermediate Similarity	NPC470945
0.7468	Intermediate Similarity	NPC472478
0.7439	Intermediate Similarity	NPC32037
0.7439	Intermediate Similarity	NPC202868
0.7436	Intermediate Similarity	NPC231739
0.7436	Intermediate Similarity	NPC192006
0.7412	Intermediate Similarity	NPC472325
0.7412	Intermediate Similarity	NPC477711
0.7407	Intermediate Similarity	NPC62214
0.7407	Intermediate Similarity	NPC52609
0.7407	Intermediate Similarity	NPC105173
0.7407	Intermediate Similarity	NPC470165
0.7407	Intermediate Similarity	NPC1761
0.7403	Intermediate Similarity	NPC215481
0.7403	Intermediate Similarity	NPC242722
0.7403	Intermediate Similarity	NPC250621
0.7397	Intermediate Similarity	NPC476614
0.7391	Intermediate Similarity	NPC243532
0.7381	Intermediate Similarity	NPC477710
0.7375	Intermediate Similarity	NPC116797
0.7375	Intermediate Similarity	NPC121984
0.7368	Intermediate Similarity	NPC144995
0.7368	Intermediate Similarity	NPC227814
0.7368	Intermediate Similarity	NPC476649
0.7349	Intermediate Similarity	NPC475022
0.7349	Intermediate Similarity	NPC472974
0.7349	Intermediate Similarity	NPC222613
0.7349	Intermediate Similarity	NPC118648
0.7349	Intermediate Similarity	NPC94666
0.7349	Intermediate Similarity	NPC194417
0.7342	Intermediate Similarity	NPC113363
0.7342	Intermediate Similarity	NPC470239
0.7342	Intermediate Similarity	NPC229204
0.7342	Intermediate Similarity	NPC470244
0.7342	Intermediate Similarity	NPC472490
0.7342	Intermediate Similarity	NPC152061
0.7333	Intermediate Similarity	NPC474884
0.7333	Intermediate Similarity	NPC288667
0.7326	Intermediate Similarity	NPC219874
0.7317	Intermediate Similarity	NPC472326
0.7317	Intermediate Similarity	NPC40687
0.7317	Intermediate Similarity	NPC476412
0.7308	Intermediate Similarity	NPC325946
0.7297	Intermediate Similarity	NPC261398
0.7294	Intermediate Similarity	NPC472973
0.7294	Intermediate Similarity	NPC123912
0.7294	Intermediate Similarity	NPC117405
0.7294	Intermediate Similarity	NPC52198
0.7286	Intermediate Similarity	NPC201939
0.7284	Intermediate Similarity	NPC93590
0.7284	Intermediate Similarity	NPC103486
0.7284	Intermediate Similarity	NPC145963
0.7284	Intermediate Similarity	NPC151519
0.7284	Intermediate Similarity	NPC212083
0.7273	Intermediate Similarity	NPC251435
0.7273	Intermediate Similarity	NPC275960
0.7273	Intermediate Similarity	NPC48803
0.7273	Intermediate Similarity	NPC193645
0.7273	Intermediate Similarity	NPC90121
0.7262	Intermediate Similarity	NPC109900
0.7262	Intermediate Similarity	NPC58063
0.726	Intermediate Similarity	NPC106613
0.725	Intermediate Similarity	NPC164218
0.725	Intermediate Similarity	NPC233377
0.725	Intermediate Similarity	NPC148685
0.725	Intermediate Similarity	NPC306095
0.725	Intermediate Similarity	NPC157895
0.725	Intermediate Similarity	NPC104120
0.7246	Intermediate Similarity	NPC278202
0.7241	Intermediate Similarity	NPC125180
0.7237	Intermediate Similarity	NPC300940
0.7237	Intermediate Similarity	NPC49737
0.7237	Intermediate Similarity	NPC261316
0.7229	Intermediate Similarity	NPC474853
0.7229	Intermediate Similarity	NPC469948
0.7229	Intermediate Similarity	NPC79573
0.7229	Intermediate Similarity	NPC179006
0.7229	Intermediate Similarity	NPC161957
0.7229	Intermediate Similarity	NPC15807
0.7222	Intermediate Similarity	NPC61473
0.7215	Intermediate Similarity	NPC297996
0.7215	Intermediate Similarity	NPC207186
0.7206	Intermediate Similarity	NPC71755
0.72	Intermediate Similarity	NPC286154
0.7195	Intermediate Similarity	NPC11620
0.7183	Intermediate Similarity	NPC477830
0.7183	Intermediate Similarity	NPC477707
0.7179	Intermediate Similarity	NPC226242
0.7179	Intermediate Similarity	NPC477708
0.7179	Intermediate Similarity	NPC271070
0.7179	Intermediate Similarity	NPC279537
0.7176	Intermediate Similarity	NPC470524
0.7176	Intermediate Similarity	NPC328539
0.7176	Intermediate Similarity	NPC474854
0.7162	Intermediate Similarity	NPC45264
0.7162	Intermediate Similarity	NPC117804
0.7162	Intermediate Similarity	NPC477452
0.7162	Intermediate Similarity	NPC469688
0.716	Intermediate Similarity	NPC119229
0.716	Intermediate Similarity	NPC90055
0.716	Intermediate Similarity	NPC470298
0.716	Intermediate Similarity	NPC473420
0.7159	Intermediate Similarity	NPC472977
0.7159	Intermediate Similarity	NPC473162
0.7159	Intermediate Similarity	NPC471207
0.7159	Intermediate Similarity	NPC472976
0.7143	Intermediate Similarity	NPC470299
0.7143	Intermediate Similarity	NPC167049
0.7143	Intermediate Similarity	NPC474778
0.7143	Intermediate Similarity	NPC474733
0.7143	Intermediate Similarity	NPC20688
0.7143	Intermediate Similarity	NPC327115
0.7143	Intermediate Similarity	NPC31564
0.7143	Intermediate Similarity	NPC469691
0.7143	Intermediate Similarity	NPC179591
0.7143	Intermediate Similarity	NPC145879
0.7143	Intermediate Similarity	NPC472966
0.7143	Intermediate Similarity	NPC474732
0.7126	Intermediate Similarity	NPC472978
0.7126	Intermediate Similarity	NPC472975
0.7126	Intermediate Similarity	NPC99380
0.7125	Intermediate Similarity	NPC469690
0.7125	Intermediate Similarity	NPC476177
0.7125	Intermediate Similarity	NPC164308
0.7125	Intermediate Similarity	NPC308545
0.7125	Intermediate Similarity	NPC82488
0.7125	Intermediate Similarity	NPC474113
0.7123	Intermediate Similarity	NPC137163
0.7111	Intermediate Similarity	NPC169205
0.7108	Intermediate Similarity	NPC161423
0.7108	Intermediate Similarity	NPC475796
0.7108	Intermediate Similarity	NPC70424
0.7108	Intermediate Similarity	NPC227064
0.7108	Intermediate Similarity	NPC214043
0.7108	Intermediate Similarity	NPC473246
0.7108	Intermediate Similarity	NPC9868
0.7108	Intermediate Similarity	NPC329043
0.7108	Intermediate Similarity	NPC221758
0.7108	Intermediate Similarity	NPC59453

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 NPC250928 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	2083
0.2-0.3	3990
0.3-0.4	2064
0.4-0.5	483
0.5-0.6	284
0.6-0.7	78
0.7-0.8	6
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
0.7606	Intermediate Similarity	NPD7331	Phase 2
0.7326	Intermediate Similarity	NPD6079	Approved
0.7284	Intermediate Similarity	NPD3667	Approved
0.7273	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5368	Approved
0.7222	Intermediate Similarity	NPD7341	Phase 2
0.7215	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4786	Approved
0.7108	Intermediate Similarity	NPD3133	Approved
0.7108	Intermediate Similarity	NPD3665	Phase 1
0.7108	Intermediate Similarity	NPD3666	Approved
0.7093	Intermediate Similarity	NPD5328	Approved
0.7073	Intermediate Similarity	NPD6435	Approved
0.7037	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4695	Discontinued
0.7024	Intermediate Similarity	NPD5363	Approved
0.7011	Intermediate Similarity	NPD5785	Approved
0.7	Intermediate Similarity	NPD5222	Approved
0.7	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5221	Approved
0.6951	Remote Similarity	NPD5369	Approved
0.6944	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3618	Phase 1
0.6941	Remote Similarity	NPD5786	Approved
0.6941	Remote Similarity	NPD5279	Phase 3
0.6932	Remote Similarity	NPD6411	Approved
0.6923	Remote Similarity	NPD5173	Approved
0.6867	Remote Similarity	NPD4270	Approved
0.6867	Remote Similarity	NPD4269	Approved
0.6849	Remote Similarity	NPD3197	Phase 1
0.6786	Remote Similarity	NPD5362	Discontinued
0.6786	Remote Similarity	NPD7154	Phase 3
0.6774	Remote Similarity	NPD5286	Approved
0.6774	Remote Similarity	NPD5285	Approved
0.6774	Remote Similarity	NPD4696	Approved
0.6705	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6101	Approved
0.6702	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD3704	Approved
0.6667	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5225	Approved
0.6632	Remote Similarity	NPD5226	Approved
0.6632	Remote Similarity	NPD5211	Phase 2
0.6632	Remote Similarity	NPD4633	Approved
0.6632	Remote Similarity	NPD5224	Approved
0.663	Remote Similarity	NPD4697	Phase 3
0.6628	Remote Similarity	NPD1696	Phase 3
0.6627	Remote Similarity	NPD4252	Approved
0.6618	Remote Similarity	NPD3172	Approved
0.6593	Remote Similarity	NPD5282	Discontinued
0.6562	Remote Similarity	NPD5175	Approved
0.6562	Remote Similarity	NPD5174	Approved
0.6559	Remote Similarity	NPD4755	Approved
0.6556	Remote Similarity	NPD7983	Approved
0.6556	Remote Similarity	NPD7515	Phase 2
0.6552	Remote Similarity	NPD5690	Phase 2
0.6522	Remote Similarity	NPD4629	Approved
0.6522	Remote Similarity	NPD4266	Approved
0.6522	Remote Similarity	NPD3194	Approved
0.6522	Remote Similarity	NPD3195	Phase 2
0.6522	Remote Similarity	NPD5210	Approved
0.6522	Remote Similarity	NPD3196	Approved
0.6517	Remote Similarity	NPD4753	Phase 2
0.6512	Remote Similarity	NPD3668	Phase 3
0.6495	Remote Similarity	NPD5141	Approved
0.6484	Remote Similarity	NPD5778	Approved
0.6484	Remote Similarity	NPD5779	Approved
0.6484	Remote Similarity	NPD4202	Approved
0.6471	Remote Similarity	NPD4221	Approved
0.6471	Remote Similarity	NPD4223	Phase 3
0.6437	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD1694	Approved
0.6429	Remote Similarity	NPD4822	Approved
0.6429	Remote Similarity	NPD4820	Approved
0.6429	Remote Similarity	NPD4821	Approved
0.6429	Remote Similarity	NPD4819	Approved
0.6421	Remote Similarity	NPD4700	Approved
0.6404	Remote Similarity	NPD4518	Approved
0.6395	Remote Similarity	NPD5331	Approved
0.6395	Remote Similarity	NPD5332	Approved
0.6395	Remote Similarity	NPD4788	Approved
0.6386	Remote Similarity	NPD4271	Approved
0.6386	Remote Similarity	NPD4268	Approved
0.6364	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5697	Approved
0.6364	Remote Similarity	NPD4519	Discontinued
0.6364	Remote Similarity	NPD4623	Approved
0.6353	Remote Similarity	NPD4790	Discontinued
0.6329	Remote Similarity	NPD7143	Approved
0.6329	Remote Similarity	NPD7144	Approved
0.6322	Remote Similarity	NPD4197	Approved
0.6304	Remote Similarity	NPD6399	Phase 3
0.63	Remote Similarity	NPD5168	Approved
0.63	Remote Similarity	NPD4729	Approved
0.63	Remote Similarity	NPD6011	Approved
0.63	Remote Similarity	NPD4730	Approved
0.63	Remote Similarity	NPD6881	Approved
0.63	Remote Similarity	NPD6899	Approved
0.6296	Remote Similarity	NPD6924	Approved
0.6296	Remote Similarity	NPD6926	Approved
0.6292	Remote Similarity	NPD3573	Approved
0.6286	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD7839	Suspended
0.6265	Remote Similarity	NPD4756	Discovery
0.6264	Remote Similarity	NPD6698	Approved
0.6264	Remote Similarity	NPD46	Approved
0.625	Remote Similarity	NPD7151	Approved
0.625	Remote Similarity	NPD5329	Approved
0.625	Remote Similarity	NPD7150	Approved
0.625	Remote Similarity	NPD7152	Approved
0.6238	Remote Similarity	NPD6012	Approved
0.6238	Remote Similarity	NPD6014	Approved
0.6238	Remote Similarity	NPD6013	Approved
0.6237	Remote Similarity	NPD7748	Approved
0.6235	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4754	Approved
0.622	Remote Similarity	NPD8264	Approved
0.622	Remote Similarity	NPD8039	Approved
0.6216	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD6922	Approved
0.6203	Remote Similarity	NPD6923	Approved
0.6197	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.619	Remote Similarity	NPD3732	Approved
0.619	Remote Similarity	NPD3617	Approved
0.618	Remote Similarity	NPD6422	Discontinued
0.618	Remote Similarity	NPD5280	Approved
0.618	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.618	Remote Similarity	NPD5330	Approved
0.618	Remote Similarity	NPD4690	Approved
0.618	Remote Similarity	NPD4693	Phase 3
0.618	Remote Similarity	NPD4138	Approved
0.618	Remote Similarity	NPD4688	Approved
0.618	Remote Similarity	NPD7146	Approved
0.618	Remote Similarity	NPD6409	Approved
0.618	Remote Similarity	NPD6684	Approved
0.618	Remote Similarity	NPD4689	Approved
0.618	Remote Similarity	NPD4694	Approved
0.618	Remote Similarity	NPD7521	Approved
0.618	Remote Similarity	NPD5205	Approved
0.618	Remote Similarity	NPD7334	Approved
0.6176	Remote Similarity	NPD4634	Approved
0.6176	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5249	Phase 3
0.6176	Remote Similarity	NPD5250	Approved
0.6176	Remote Similarity	NPD7290	Approved
0.6176	Remote Similarity	NPD5251	Approved
0.6176	Remote Similarity	NPD7102	Approved
0.6176	Remote Similarity	NPD5247	Approved
0.6176	Remote Similarity	NPD5135	Approved
0.6176	Remote Similarity	NPD5169	Approved
0.6176	Remote Similarity	NPD6883	Approved
0.6176	Remote Similarity	NPD5248	Approved
0.6145	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD6933	Approved
0.6139	Remote Similarity	NPD5128	Approved
0.6133	Remote Similarity	NPD368	Approved
0.6125	Remote Similarity	NPD4691	Approved
0.6119	Remote Similarity	NPD622	Approved
0.6118	Remote Similarity	NPD4195	Approved
0.6117	Remote Similarity	NPD5127	Approved
0.6117	Remote Similarity	NPD6847	Approved
0.6117	Remote Similarity	NPD5217	Approved
0.6117	Remote Similarity	NPD6649	Approved
0.6117	Remote Similarity	NPD5215	Approved
0.6117	Remote Similarity	NPD6617	Approved
0.6117	Remote Similarity	NPD6869	Approved
0.6117	Remote Similarity	NPD6650	Approved
0.6117	Remote Similarity	NPD5216	Approved
0.6117	Remote Similarity	NPD8130	Phase 1
0.61	Remote Similarity	NPD4768	Approved
0.61	Remote Similarity	NPD5739	Approved
0.61	Remote Similarity	NPD7128	Approved
0.61	Remote Similarity	NPD6675	Approved
0.61	Remote Similarity	NPD6402	Approved
0.61	Remote Similarity	NPD4767	Approved
0.6098	Remote Similarity	NPD4058	Approved
0.6092	Remote Similarity	NPD5209	Approved
0.6092	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD28	Approved
0.6087	Remote Similarity	NPD29	Approved
0.6071	Remote Similarity	NPD6932	Approved
0.6058	Remote Similarity	NPD6882	Approved
0.6058	Remote Similarity	NPD8297	Approved
0.6044	Remote Similarity	NPD6903	Approved
0.6044	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD7902	Approved
0.6042	Remote Similarity	NPD6084	Phase 2
0.6042	Remote Similarity	NPD6083	Phase 2
0.604	Remote Similarity	NPD5701	Approved
0.6029	Remote Similarity	NPD3173	Approved
0.6024	Remote Similarity	NPD7339	Approved
0.6024	Remote Similarity	NPD6942	Approved
0.6022	Remote Similarity	NPD5281	Approved
0.6022	Remote Similarity	NPD5284	Approved
0.6	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD4137	Phase 3
0.6	Remote Similarity	NPD7145	Approved
0.6	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.598	Remote Similarity	NPD7320	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