NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	334.21
Volume:	367.898
LogP:	3.32
LogD:	1.853
LogS:	-3.654
# Rotatable Bonds:	8
TPSA:	71.44
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.418
Synthetic Accessibility Score:	4.465
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.496
MDCK Permeability:	2.30E-05
Pgp-inhibitor:	0.9
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.056
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.547
Plasma Protein Binding (PPB):	92.78%
Volume Distribution (VD):	0.704
Pgp-substrate:	7.79%

ADMET: Metabolism

CYP1A2-inhibitor:	0.108
CYP1A2-substrate:	0.4
CYP2C19-inhibitor:	0.411
CYP2C19-substrate:	0.811
CYP2C9-inhibitor:	0.334
CYP2C9-substrate:	0.27
CYP2D6-inhibitor:	0.15
CYP2D6-substrate:	0.123
CYP3A4-inhibitor:	0.545
CYP3A4-substrate:	0.31

ADMET: Excretion

Clearance (CL):	11.662
Half-life (T1/2):	0.689

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.188
Drug-inuced Liver Injury (DILI):	0.152
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.373
Maximum Recommended Daily Dose:	0.535
Skin Sensitization:	0.817
Carcinogencity:	0.868
Eye Corrosion:	0.871
Eye Irritation:	0.65
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC478122

Natural Product ID:	NPC478122
*Common Name:**	Rel-Trigohetone
IUPAC Name:	6-[(2S,5E)-2,7-dihydroxy-6,10-dimethyl-8-oxoundeca-5,9-dien-2-yl]-3-methylcyclohex-2-en-1-one
Synonyms:	Rel-Trigohetone
Standard InCHIKey:	MMCHYQXMIUOBDF-DZFGGSJHSA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-13(2)11-18(22)19(23)15(4)7-6-10-20(5,24)16-9-8-14(3)12-17(16)21/h7,11-12,16,19,23-24H,6,8-10H2,1-5H3/b15-7+/t16?,19?,20-/m0/s1
SMILES:	CC1=CC(=O)C(CC1)[C@](C)(CC/C=C(\C)/C(C(=O)C=C(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	57402797
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
NPO6609	Trigonostemon heterophyllus	Species	Euphorbiaceae	Eukaryota	n.a.	twig	n.a.	PMID[22122667]
NPO6609	Trigonostemon heterophyllus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22122667]
NPO6609	Trigonostemon heterophyllus	Species	Euphorbiaceae	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
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000	nM	PMID[22122667]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000	nM	PMID[22122667]

☑ 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 NPC478122 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	175
0.1-0.2	1173
0.2-0.3	5770
0.3-0.4	14385
0.4-0.5	11124
0.5-0.6	6612
0.6-0.7	2976
0.7-0.8	458
0.8-0.85	16
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8415	Intermediate Similarity	NPC187529
0.8395	Intermediate Similarity	NPC477785
0.8395	Intermediate Similarity	NPC477784
0.8395	Intermediate Similarity	NPC477786
0.8228	Intermediate Similarity	NPC475994
0.8228	Intermediate Similarity	NPC231739
0.8193	Intermediate Similarity	NPC474853
0.8193	Intermediate Similarity	NPC179006
0.8148	Intermediate Similarity	NPC275766
0.8101	Intermediate Similarity	NPC97173
0.8101	Intermediate Similarity	NPC471061
0.8077	Intermediate Similarity	NPC474885
0.8052	Intermediate Similarity	NPC275098
0.8	Intermediate Similarity	NPC220930
0.8	Intermediate Similarity	NPC272039
0.7976	Intermediate Similarity	NPC255174
0.7976	Intermediate Similarity	NPC79573
0.7949	Intermediate Similarity	NPC122244
0.7931	Intermediate Similarity	NPC477684
0.7922	Intermediate Similarity	NPC474884
0.7907	Intermediate Similarity	NPC53454
0.7882	Intermediate Similarity	NPC194417
0.7882	Intermediate Similarity	NPC472009
0.7875	Intermediate Similarity	NPC473536
0.7875	Intermediate Similarity	NPC476007
0.7875	Intermediate Similarity	NPC82666
0.7841	Intermediate Similarity	NPC172101
0.7821	Intermediate Similarity	NPC186042
0.7802	Intermediate Similarity	NPC471916
0.7792	Intermediate Similarity	NPC286154
0.7791	Intermediate Similarity	NPC472007
0.7791	Intermediate Similarity	NPC471738
0.7765	Intermediate Similarity	NPC15807
0.7765	Intermediate Similarity	NPC70685
0.7722	Intermediate Similarity	NPC215050
0.7711	Intermediate Similarity	NPC116797
0.7701	Intermediate Similarity	NPC472008
0.7701	Intermediate Similarity	NPC474854
0.7683	Intermediate Similarity	NPC308038
0.7683	Intermediate Similarity	NPC19900
0.7683	Intermediate Similarity	NPC281138
0.7674	Intermediate Similarity	NPC196381
0.7674	Intermediate Similarity	NPC472974
0.7674	Intermediate Similarity	NPC470955
0.7674	Intermediate Similarity	NPC476043
0.7674	Intermediate Similarity	NPC261721
0.7667	Intermediate Similarity	NPC53685
0.7625	Intermediate Similarity	NPC199445
0.7619	Intermediate Similarity	NPC279186
0.7595	Intermediate Similarity	NPC29542
0.7595	Intermediate Similarity	NPC323437
0.7595	Intermediate Similarity	NPC201562
0.759	Intermediate Similarity	NPC157895
0.759	Intermediate Similarity	NPC45495
0.759	Intermediate Similarity	NPC104120
0.759	Intermediate Similarity	NPC148685
0.759	Intermediate Similarity	NPC172013
0.759	Intermediate Similarity	NPC271104
0.7586	Intermediate Similarity	NPC23622
0.7582	Intermediate Similarity	NPC91408
0.7579	Intermediate Similarity	NPC131366
0.7564	Intermediate Similarity	NPC107848
0.7561	Intermediate Similarity	NPC192006
0.7561	Intermediate Similarity	NPC178852
0.7558	Intermediate Similarity	NPC261380
0.7558	Intermediate Similarity	NPC476426
0.7553	Intermediate Similarity	NPC207885
0.7531	Intermediate Similarity	NPC472305
0.7531	Intermediate Similarity	NPC7629
0.7531	Intermediate Similarity	NPC263582
0.7531	Intermediate Similarity	NPC151622
0.7531	Intermediate Similarity	NPC469646
0.7529	Intermediate Similarity	NPC16488
0.75	Intermediate Similarity	NPC137163
0.75	Intermediate Similarity	NPC307298
0.75	Intermediate Similarity	NPC6663
0.75	Intermediate Similarity	NPC470298
0.75	Intermediate Similarity	NPC112868
0.7473	Intermediate Similarity	NPC474882
0.7471	Intermediate Similarity	NPC316426
0.7471	Intermediate Similarity	NPC94666
0.7471	Intermediate Similarity	NPC202394
0.7471	Intermediate Similarity	NPC203795
0.7471	Intermediate Similarity	NPC315395
0.747	Intermediate Similarity	NPC7232
0.7468	Intermediate Similarity	NPC67076
0.7468	Intermediate Similarity	NPC126061
0.7468	Intermediate Similarity	NPC319163
0.7444	Intermediate Similarity	NPC73457
0.7444	Intermediate Similarity	NPC142838
0.7444	Intermediate Similarity	NPC116726
0.7442	Intermediate Similarity	NPC7927
0.7442	Intermediate Similarity	NPC472326
0.7442	Intermediate Similarity	NPC476412
0.7442	Intermediate Similarity	NPC230527
0.7439	Intermediate Similarity	NPC211279
0.7439	Intermediate Similarity	NPC203403
0.7439	Intermediate Similarity	NPC74995
0.7439	Intermediate Similarity	NPC34110
0.7439	Intermediate Similarity	NPC197659
0.7439	Intermediate Similarity	NPC325946
0.7432	Intermediate Similarity	NPC321867
0.7432	Intermediate Similarity	NPC207007
0.7432	Intermediate Similarity	NPC68679
0.7419	Intermediate Similarity	NPC471694
0.7416	Intermediate Similarity	NPC472688
0.7416	Intermediate Similarity	NPC472676
0.7416	Intermediate Similarity	NPC472983
0.7412	Intermediate Similarity	NPC7414
0.7412	Intermediate Similarity	NPC103486
0.7412	Intermediate Similarity	NPC158411
0.7412	Intermediate Similarity	NPC38796
0.7412	Intermediate Similarity	NPC93590
0.7412	Intermediate Similarity	NPC85772
0.7407	Intermediate Similarity	NPC114236
0.7407	Intermediate Similarity	NPC60718
0.7407	Intermediate Similarity	NPC474011
0.7403	Intermediate Similarity	NPC106613
0.7403	Intermediate Similarity	NPC269985
0.7396	Intermediate Similarity	NPC297281
0.7396	Intermediate Similarity	NPC473144
0.7391	Intermediate Similarity	NPC476245
0.7386	Intermediate Similarity	NPC312561
0.7381	Intermediate Similarity	NPC470946
0.7381	Intermediate Similarity	NPC138492
0.7381	Intermediate Similarity	NPC472301
0.7381	Intermediate Similarity	NPC74086
0.7381	Intermediate Similarity	NPC470945
0.7381	Intermediate Similarity	NPC306095
0.7381	Intermediate Similarity	NPC2482
0.7381	Intermediate Similarity	NPC115418
0.7381	Intermediate Similarity	NPC233352
0.7381	Intermediate Similarity	NPC471514
0.7381	Intermediate Similarity	NPC470947
0.7381	Intermediate Similarity	NPC824
0.7368	Intermediate Similarity	NPC112613
0.7368	Intermediate Similarity	NPC474329
0.7368	Intermediate Similarity	NPC469851
0.7368	Intermediate Similarity	NPC474304
0.7363	Intermediate Similarity	NPC469645
0.7363	Intermediate Similarity	NPC469692
0.7356	Intermediate Similarity	NPC32037
0.7356	Intermediate Similarity	NPC125290
0.7349	Intermediate Similarity	NPC297996
0.7349	Intermediate Similarity	NPC321180
0.7349	Intermediate Similarity	NPC471409
0.7349	Intermediate Similarity	NPC248624
0.7349	Intermediate Similarity	NPC62336
0.7349	Intermediate Similarity	NPC275494
0.7349	Intermediate Similarity	NPC121200
0.7349	Intermediate Similarity	NPC207772
0.7342	Intermediate Similarity	NPC318766
0.7342	Intermediate Similarity	NPC173321
0.7342	Intermediate Similarity	NPC203819
0.734	Intermediate Similarity	NPC316598
0.734	Intermediate Similarity	NPC166770
0.7333	Intermediate Similarity	NPC471399
0.7333	Intermediate Similarity	NPC281942
0.7333	Intermediate Similarity	NPC230332
0.7333	Intermediate Similarity	NPC113393
0.7333	Intermediate Similarity	NPC232426
0.7333	Intermediate Similarity	NPC134321
0.7333	Intermediate Similarity	NPC48010
0.7333	Intermediate Similarity	NPC473099
0.7326	Intermediate Similarity	NPC297398
0.7326	Intermediate Similarity	NPC62214
0.7326	Intermediate Similarity	NPC110150
0.7326	Intermediate Similarity	NPC66764
0.7317	Intermediate Similarity	NPC279537
0.7317	Intermediate Similarity	NPC470525
0.7317	Intermediate Similarity	NPC271070
0.7312	Intermediate Similarity	NPC94337
0.7312	Intermediate Similarity	NPC184065
0.7308	Intermediate Similarity	NPC117804
0.7308	Intermediate Similarity	NPC469688
0.7308	Intermediate Similarity	NPC45264
0.7303	Intermediate Similarity	NPC471791
0.7303	Intermediate Similarity	NPC72397
0.7303	Intermediate Similarity	NPC471793
0.7303	Intermediate Similarity	NPC7280
0.7303	Intermediate Similarity	NPC229612
0.7303	Intermediate Similarity	NPC476796
0.7297	Intermediate Similarity	NPC66020
0.7294	Intermediate Similarity	NPC14151
0.7294	Intermediate Similarity	NPC47031
0.7294	Intermediate Similarity	NPC55869
0.7294	Intermediate Similarity	NPC121984
0.7294	Intermediate Similarity	NPC67254
0.7294	Intermediate Similarity	NPC136150
0.7292	Intermediate Similarity	NPC87351
0.7292	Intermediate Similarity	NPC39996
0.7284	Intermediate Similarity	NPC7382
0.7283	Intermediate Similarity	NPC78159
0.7283	Intermediate Similarity	NPC472976
0.7283	Intermediate Similarity	NPC121825
0.7283	Intermediate Similarity	NPC472977
0.7283	Intermediate Similarity	NPC217624
0.7283	Intermediate Similarity	NPC469632
0.7283	Intermediate Similarity	NPC196227
0.7283	Intermediate Similarity	NPC8993

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 NPC478122 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1770
0.2-0.3	3991
0.3-0.4	2232
0.4-0.5	618
0.5-0.6	277
0.6-0.7	83
0.7-0.8	18
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
0.7558	Intermediate Similarity	NPD5363	Approved
0.7432	Intermediate Similarity	NPD368	Approved
0.7412	Intermediate Similarity	NPD4270	Approved
0.7412	Intermediate Similarity	NPD4269	Approved
0.7381	Intermediate Similarity	NPD4252	Approved
0.7381	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD1696	Phase 3
0.7326	Intermediate Similarity	NPD6110	Phase 1
0.7273	Intermediate Similarity	NPD7331	Phase 2
0.7222	Intermediate Similarity	NPD4753	Phase 2
0.7176	Intermediate Similarity	NPD4695	Discontinued
0.7143	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5785	Approved
0.7105	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5282	Discontinued
0.7093	Intermediate Similarity	NPD5369	Approved
0.7079	Intermediate Similarity	NPD5786	Approved
0.7079	Intermediate Similarity	NPD5279	Phase 3
0.7051	Intermediate Similarity	NPD3704	Approved
0.7045	Intermediate Similarity	NPD3666	Approved
0.7045	Intermediate Similarity	NPD3133	Approved
0.7045	Intermediate Similarity	NPD3665	Phase 1
0.7024	Intermediate Similarity	NPD4756	Discovery
0.7011	Intermediate Similarity	NPD3667	Approved
0.6989	Remote Similarity	NPD5778	Approved
0.6989	Remote Similarity	NPD5779	Approved
0.6977	Remote Similarity	NPD4822	Approved
0.6977	Remote Similarity	NPD4819	Approved
0.6977	Remote Similarity	NPD4821	Approved
0.6977	Remote Similarity	NPD4820	Approved
0.6939	Remote Similarity	NPD5211	Phase 2
0.6932	Remote Similarity	NPD5362	Discontinued
0.6923	Remote Similarity	NPD7341	Phase 2
0.6889	Remote Similarity	NPD3618	Phase 1
0.6889	Remote Similarity	NPD4519	Discontinued
0.6889	Remote Similarity	NPD4623	Approved
0.6875	Remote Similarity	NPD4755	Approved
0.6854	Remote Similarity	NPD4786	Approved
0.6854	Remote Similarity	NPD4197	Approved
0.6842	Remote Similarity	NPD5210	Approved
0.6842	Remote Similarity	NPD4629	Approved
0.6818	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5141	Approved
0.6778	Remote Similarity	NPD5329	Approved
0.6771	Remote Similarity	NPD4697	Phase 3
0.6771	Remote Similarity	NPD5221	Approved
0.6771	Remote Similarity	NPD5222	Approved
0.6771	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4268	Approved
0.6744	Remote Similarity	NPD4271	Approved
0.6742	Remote Similarity	NPD7154	Phase 3
0.6742	Remote Similarity	NPD5331	Approved
0.6742	Remote Similarity	NPD5332	Approved
0.6735	Remote Similarity	NPD4700	Approved
0.6735	Remote Similarity	NPD5286	Approved
0.6735	Remote Similarity	NPD4696	Approved
0.6735	Remote Similarity	NPD5285	Approved
0.6705	Remote Similarity	NPD4790	Discontinued
0.6703	Remote Similarity	NPD5280	Approved
0.6703	Remote Similarity	NPD5690	Phase 2
0.6703	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4694	Approved
0.6702	Remote Similarity	NPD7515	Phase 2
0.6701	Remote Similarity	NPD5173	Approved
0.6701	Remote Similarity	NPD6083	Phase 2
0.6701	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD5223	Approved
0.6632	Remote Similarity	NPD4202	Approved
0.6629	Remote Similarity	NPD4221	Approved
0.6629	Remote Similarity	NPD4223	Phase 3
0.6622	Remote Similarity	NPD342	Phase 1
0.66	Remote Similarity	NPD5225	Approved
0.66	Remote Similarity	NPD5226	Approved
0.66	Remote Similarity	NPD5224	Approved
0.66	Remote Similarity	NPD4633	Approved
0.6596	Remote Similarity	NPD46	Approved
0.6596	Remote Similarity	NPD6698	Approved
0.6591	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD8264	Approved
0.6552	Remote Similarity	NPD3617	Approved
0.6535	Remote Similarity	NPD5174	Approved
0.6535	Remote Similarity	NPD4754	Approved
0.6535	Remote Similarity	NPD5175	Approved
0.6526	Remote Similarity	NPD7983	Approved
0.6526	Remote Similarity	NPD6079	Approved
0.6526	Remote Similarity	NPD7637	Suspended
0.6526	Remote Similarity	NPD6411	Approved
0.6526	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5370	Suspended
0.6489	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD3668	Phase 3
0.6476	Remote Similarity	NPD4634	Approved
0.6465	Remote Similarity	NPD5696	Approved
0.6465	Remote Similarity	NPD4225	Approved
0.6444	Remote Similarity	NPD5209	Approved
0.6429	Remote Similarity	NPD7839	Suspended
0.6422	Remote Similarity	NPD7115	Discovery
0.642	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6402	Approved
0.6408	Remote Similarity	NPD4768	Approved
0.6408	Remote Similarity	NPD7128	Approved
0.6408	Remote Similarity	NPD4767	Approved
0.6408	Remote Similarity	NPD5739	Approved
0.6408	Remote Similarity	NPD6675	Approved
0.6404	Remote Similarity	NPD5368	Approved
0.6392	Remote Similarity	NPD7748	Approved
0.6383	Remote Similarity	NPD5737	Approved
0.6383	Remote Similarity	NPD6672	Approved
0.6364	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5697	Approved
0.6346	Remote Similarity	NPD5701	Approved
0.6344	Remote Similarity	NPD4689	Approved
0.6344	Remote Similarity	NPD4690	Approved
0.6344	Remote Similarity	NPD4138	Approved
0.6344	Remote Similarity	NPD4688	Approved
0.6344	Remote Similarity	NPD5205	Approved
0.6344	Remote Similarity	NPD4693	Phase 3
0.6321	Remote Similarity	NPD6371	Approved
0.6304	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6399	Phase 3
0.6286	Remote Similarity	NPD6881	Approved
0.6286	Remote Similarity	NPD7320	Approved
0.6286	Remote Similarity	NPD6899	Approved
0.6286	Remote Similarity	NPD4730	Approved
0.6286	Remote Similarity	NPD6011	Approved
0.6286	Remote Similarity	NPD5128	Approved
0.6286	Remote Similarity	NPD4729	Approved
0.6264	Remote Similarity	NPD6435	Approved
0.6238	Remote Similarity	NPD7640	Approved
0.6238	Remote Similarity	NPD7639	Approved
0.6237	Remote Similarity	NPD1694	Approved
0.6226	Remote Similarity	NPD6013	Approved
0.6226	Remote Similarity	NPD6372	Approved
0.6226	Remote Similarity	NPD6014	Approved
0.6226	Remote Similarity	NPD6012	Approved
0.6226	Remote Similarity	NPD6373	Approved
0.6222	Remote Similarity	NPD7332	Phase 2
0.6222	Remote Similarity	NPD7514	Phase 3
0.6211	Remote Similarity	NPD4518	Approved
0.6203	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7902	Approved
0.619	Remote Similarity	NPD4137	Phase 3
0.6186	Remote Similarity	NPD5281	Approved
0.6186	Remote Similarity	NPD5284	Approved
0.6186	Remote Similarity	NPD5693	Phase 1
0.6184	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD3197	Phase 1
0.617	Remote Similarity	NPD7334	Approved
0.617	Remote Similarity	NPD5330	Approved
0.617	Remote Similarity	NPD6684	Approved
0.617	Remote Similarity	NPD4249	Approved
0.617	Remote Similarity	NPD7146	Approved
0.617	Remote Similarity	NPD7521	Approved
0.617	Remote Similarity	NPD6409	Approved
0.6168	Remote Similarity	NPD5250	Approved
0.6168	Remote Similarity	NPD5169	Approved
0.6168	Remote Similarity	NPD7290	Approved
0.6168	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD7102	Approved
0.6168	Remote Similarity	NPD5248	Approved
0.6168	Remote Similarity	NPD5251	Approved
0.6168	Remote Similarity	NPD5135	Approved
0.6168	Remote Similarity	NPD5247	Approved
0.6168	Remote Similarity	NPD6883	Approved
0.6168	Remote Similarity	NPD5249	Phase 3
0.6154	Remote Similarity	NPD287	Approved
0.6146	Remote Similarity	NPD6673	Approved
0.6146	Remote Similarity	NPD6904	Approved
0.6146	Remote Similarity	NPD6080	Approved
0.6145	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7638	Approved
0.6136	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD5168	Approved
0.6122	Remote Similarity	NPD5133	Approved
0.6118	Remote Similarity	NPD4747	Approved
0.6118	Remote Similarity	NPD4691	Approved
0.6111	Remote Similarity	NPD5215	Approved
0.6111	Remote Similarity	NPD6847	Approved
0.6111	Remote Similarity	NPD6649	Approved
0.6111	Remote Similarity	NPD6869	Approved
0.6111	Remote Similarity	NPD6617	Approved
0.6111	Remote Similarity	NPD5217	Approved
0.6111	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4195	Approved
0.6111	Remote Similarity	NPD6650	Approved
0.6111	Remote Similarity	NPD5127	Approved
0.6111	Remote Similarity	NPD5216	Approved
0.6111	Remote Similarity	NPD8130	Phase 1
0.6105	Remote Similarity	NPD4251	Approved
0.6105	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD4250	Approved
0.6092	Remote Similarity	NPD6924	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