NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	208.15
Volume:	234.519
LogP:	2.367
LogD:	1.563
LogS:	-2.532
# Rotatable Bonds:	2
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.708
Synthetic Accessibility Score:	3.37
Fsp3:	0.615
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:	-4.614
MDCK Permeability:	2.9394528610282578e-05
Pgp-inhibitor:	0.617
Pgp-substrate:	0.699
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.595
Plasma Protein Binding (PPB):	83.59571838378906%
Volume Distribution (VD):	2.182
Pgp-substrate:	19.8463077545166%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.177
CYP2C19-inhibitor:	0.1
CYP2C19-substrate:	0.89
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.444
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.636
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.662

ADMET: Excretion

Clearance (CL):	5.399
Half-life (T1/2):	0.727

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.293
Drug-inuced Liver Injury (DILI):	0.114
AMES Toxicity:	0.398
Rat Oral Acute Toxicity:	0.667
Maximum Recommended Daily Dose:	0.894
Skin Sensitization:	0.653
Carcinogencity:	0.914
Eye Corrosion:	0.053
Eye Irritation:	0.514
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC117804

Natural Product ID:	NPC117804
*Common Name:**	(E)-4-((1R,4R)-4-Hydroxy-2,6,6-Trimethylcyclohex-2-Enyl)But-3-En-2-One
IUPAC Name:	(E)-4-[(1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one
Synonyms:
Standard InCHIKey:	FDSNVAKZRJLMJN-WTIVYXKASA-N
Standard InCHI:	InChI=1S/C13H20O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5-7,11-12,15H,8H2,1-4H3/b6-5+/t11-,12-/m0/s1
SMILES:	CC1=C[C@@H](CC(C)(C)[C@H]1/C=C/C(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458125
PubChem CID:	10889124
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
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387648]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[29254897]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16333	Chenopodium album	Species	Chenopodiaceae	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
NPT364	Organism	Lactuca sativa	Lactuca sativa	Inhibition	=	30.0	%	PMID[522217]

☑ 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 NPC117804 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	145
0.1-0.2	1345
0.2-0.3	7910
0.3-0.4	17362
0.4-0.5	8278
0.5-0.6	5711
0.6-0.7	1695
0.7-0.8	223
0.8-0.85	18
0.85-0.9	7
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC95863
0.9118	High Similarity	NPC186042
0.863	High Similarity	NPC19900
0.8571	High Similarity	NPC201562
0.8571	High Similarity	NPC29542
0.8571	High Similarity	NPC323437
0.8493	Intermediate Similarity	NPC475994
0.8451	Intermediate Similarity	NPC215050
0.8382	Intermediate Similarity	NPC106613
0.8356	Intermediate Similarity	NPC203403
0.8289	Intermediate Similarity	NPC158411
0.8289	Intermediate Similarity	NPC38796
0.8254	Intermediate Similarity	NPC48891
0.8158	Intermediate Similarity	NPC6663
0.8143	Intermediate Similarity	NPC136473
0.8133	Intermediate Similarity	NPC308038
0.8116	Intermediate Similarity	NPC269985
0.8108	Intermediate Similarity	NPC149550
0.8108	Intermediate Similarity	NPC85105
0.8026	Intermediate Similarity	NPC471514
0.8	Intermediate Similarity	NPC62336
0.7975	Intermediate Similarity	NPC476426
0.7973	Intermediate Similarity	NPC263582
0.791	Intermediate Similarity	NPC269737
0.7887	Intermediate Similarity	NPC471560
0.7875	Intermediate Similarity	NPC194417
0.7867	Intermediate Similarity	NPC476007
0.7867	Intermediate Similarity	NPC74995
0.7857	Intermediate Similarity	NPC114651
0.7846	Intermediate Similarity	NPC71755
0.7838	Intermediate Similarity	NPC474885
0.7838	Intermediate Similarity	NPC114236
0.7821	Intermediate Similarity	NPC93590
0.7808	Intermediate Similarity	NPC153660
0.7792	Intermediate Similarity	NPC45495
0.7778	Intermediate Similarity	NPC286154
0.7778	Intermediate Similarity	NPC34834
0.7778	Intermediate Similarity	NPC14002
0.775	Intermediate Similarity	NPC109528
0.7746	Intermediate Similarity	NPC471238
0.7733	Intermediate Similarity	NPC470525
0.7733	Intermediate Similarity	NPC250621
0.7722	Intermediate Similarity	NPC79945
0.7703	Intermediate Similarity	NPC227814
0.7703	Intermediate Similarity	NPC144995
0.7692	Intermediate Similarity	NPC6434
0.7681	Intermediate Similarity	NPC107540
0.7671	Intermediate Similarity	NPC474884
0.7671	Intermediate Similarity	NPC319163
0.7671	Intermediate Similarity	NPC67076
0.7662	Intermediate Similarity	NPC152061
0.7662	Intermediate Similarity	NPC7232
0.7656	Intermediate Similarity	NPC5626
0.7654	Intermediate Similarity	NPC472974
0.7647	Intermediate Similarity	NPC207007
0.7647	Intermediate Similarity	NPC321867
0.7647	Intermediate Similarity	NPC68679
0.7639	Intermediate Similarity	NPC474248
0.7639	Intermediate Similarity	NPC473893
0.7625	Intermediate Similarity	NPC476412
0.76	Intermediate Similarity	NPC313179
0.76	Intermediate Similarity	NPC69383
0.76	Intermediate Similarity	NPC171148
0.7595	Intermediate Similarity	NPC279186
0.7595	Intermediate Similarity	NPC224455
0.7564	Intermediate Similarity	NPC281880
0.7564	Intermediate Similarity	NPC157895
0.7564	Intermediate Similarity	NPC104120
0.7564	Intermediate Similarity	NPC172013
0.7564	Intermediate Similarity	NPC271104
0.7564	Intermediate Similarity	NPC148685
0.7538	Intermediate Similarity	NPC251666
0.7538	Intermediate Similarity	NPC232247
0.7538	Intermediate Similarity	NPC317899
0.7532	Intermediate Similarity	NPC172066
0.7531	Intermediate Similarity	NPC179006
0.7531	Intermediate Similarity	NPC474853
0.75	Intermediate Similarity	NPC66020
0.75	Intermediate Similarity	NPC57370
0.75	Intermediate Similarity	NPC253190
0.75	Intermediate Similarity	NPC472377
0.75	Intermediate Similarity	NPC23117
0.75	Intermediate Similarity	NPC96484
0.7468	Intermediate Similarity	NPC159148
0.7465	Intermediate Similarity	NPC267027
0.7465	Intermediate Similarity	NPC202017
0.7463	Intermediate Similarity	NPC155025
0.7463	Intermediate Similarity	NPC311852
0.7439	Intermediate Similarity	NPC472986
0.7439	Intermediate Similarity	NPC472985
0.7436	Intermediate Similarity	NPC281138
0.7436	Intermediate Similarity	NPC170394
0.7432	Intermediate Similarity	NPC471272
0.7432	Intermediate Similarity	NPC471268
0.7432	Intermediate Similarity	NPC477792
0.7432	Intermediate Similarity	NPC471271
0.7429	Intermediate Similarity	NPC290367
0.7429	Intermediate Similarity	NPC96793
0.7429	Intermediate Similarity	NPC323424
0.7407	Intermediate Similarity	NPC33913
0.7407	Intermediate Similarity	NPC302360
0.7407	Intermediate Similarity	NPC230527
0.7407	Intermediate Similarity	NPC7927
0.7403	Intermediate Similarity	NPC471061
0.7403	Intermediate Similarity	NPC91594
0.7403	Intermediate Similarity	NPC97377
0.7403	Intermediate Similarity	NPC197659
0.7403	Intermediate Similarity	NPC470428
0.7381	Intermediate Similarity	NPC472973
0.7381	Intermediate Similarity	NPC123912
0.7381	Intermediate Similarity	NPC472983
0.7368	Intermediate Similarity	NPC166018
0.7368	Intermediate Similarity	NPC169056
0.7368	Intermediate Similarity	NPC225665
0.7361	Intermediate Similarity	NPC68703
0.7361	Intermediate Similarity	NPC69649
0.7361	Intermediate Similarity	NPC96962
0.7361	Intermediate Similarity	NPC171225
0.7353	Intermediate Similarity	NPC475931
0.7349	Intermediate Similarity	NPC287079
0.7344	Intermediate Similarity	NPC35756
0.7333	Intermediate Similarity	NPC130665
0.7333	Intermediate Similarity	NPC275098
0.7326	Intermediate Similarity	NPC474736
0.7317	Intermediate Similarity	NPC471267
0.7313	Intermediate Similarity	NPC268185
0.7308	Intermediate Similarity	NPC167891
0.7308	Intermediate Similarity	NPC275494
0.7308	Intermediate Similarity	NPC83351
0.7308	Intermediate Similarity	NPC297996
0.7308	Intermediate Similarity	NPC476949
0.7308	Intermediate Similarity	NPC471409
0.7308	Intermediate Similarity	NPC478122
0.7297	Intermediate Similarity	NPC203819
0.7286	Intermediate Similarity	NPC473759
0.7286	Intermediate Similarity	NPC474155
0.7284	Intermediate Similarity	NPC311070
0.7284	Intermediate Similarity	NPC105173
0.7273	Intermediate Similarity	NPC130209
0.7273	Intermediate Similarity	NPC148216
0.7273	Intermediate Similarity	NPC265588
0.7273	Intermediate Similarity	NPC469646
0.7273	Intermediate Similarity	NPC148163
0.7262	Intermediate Similarity	NPC474854
0.7262	Intermediate Similarity	NPC7280
0.7262	Intermediate Similarity	NPC229612
0.726	Intermediate Similarity	NPC45264
0.725	Intermediate Similarity	NPC136150
0.725	Intermediate Similarity	NPC116797
0.7246	Intermediate Similarity	NPC99487
0.7237	Intermediate Similarity	NPC306727
0.7237	Intermediate Similarity	NPC78527
0.7222	Intermediate Similarity	NPC137163
0.7222	Intermediate Similarity	NPC326310
0.7215	Intermediate Similarity	NPC242767
0.7215	Intermediate Similarity	NPC470429
0.7209	Intermediate Similarity	NPC472978
0.7209	Intermediate Similarity	NPC475806
0.7206	Intermediate Similarity	NPC181872
0.7206	Intermediate Similarity	NPC226848
0.72	Intermediate Similarity	NPC242001
0.72	Intermediate Similarity	NPC23954
0.7195	Intermediate Similarity	NPC472265
0.7195	Intermediate Similarity	NPC472326
0.7183	Intermediate Similarity	NPC300593
0.7179	Intermediate Similarity	NPC86917
0.7179	Intermediate Similarity	NPC82666
0.7179	Intermediate Similarity	NPC257666
0.7179	Intermediate Similarity	NPC262747
0.7179	Intermediate Similarity	NPC266193
0.7179	Intermediate Similarity	NPC325946
0.7176	Intermediate Similarity	NPC309603
0.7176	Intermediate Similarity	NPC314727
0.7176	Intermediate Similarity	NPC146554
0.7176	Intermediate Similarity	NPC262858
0.7176	Intermediate Similarity	NPC473999
0.7176	Intermediate Similarity	NPC472240
0.7162	Intermediate Similarity	NPC10758
0.7162	Intermediate Similarity	NPC250928
0.716	Intermediate Similarity	NPC256112
0.716	Intermediate Similarity	NPC2524
0.716	Intermediate Similarity	NPC103486
0.716	Intermediate Similarity	NPC92226
0.7159	Intermediate Similarity	NPC476245
0.7143	Intermediate Similarity	NPC475251
0.7143	Intermediate Similarity	NPC260573
0.7143	Intermediate Similarity	NPC474011
0.7143	Intermediate Similarity	NPC476346
0.7143	Intermediate Similarity	NPC312561
0.7126	Intermediate Similarity	NPC109305
0.7125	Intermediate Similarity	NPC306095
0.7125	Intermediate Similarity	NPC96362
0.7125	Intermediate Similarity	NPC472301
0.7125	Intermediate Similarity	NPC234193
0.7125	Intermediate Similarity	NPC472478
0.7125	Intermediate Similarity	NPC2482
0.7125	Intermediate Similarity	NPC160582
0.7123	Intermediate Similarity	NPC477791
0.7108	Intermediate Similarity	NPC255174
0.7108	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 NPC117804 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	135
0.1-0.2	1881
0.2-0.3	4357
0.3-0.4	2071
0.4-0.5	418
0.5-0.6	238
0.6-0.7	46
0.7-0.8	3
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7647	Intermediate Similarity	NPD368	Approved
0.76	Intermediate Similarity	NPD8264	Approved
0.7273	Intermediate Similarity	NPD342	Phase 1
0.7108	Intermediate Similarity	NPD1696	Phase 3
0.7	Intermediate Similarity	NPD4195	Approved
0.6988	Remote Similarity	NPD3666	Approved
0.6988	Remote Similarity	NPD3665	Phase 1
0.6988	Remote Similarity	NPD3133	Approved
0.6912	Remote Similarity	NPD4219	Approved
0.6901	Remote Similarity	NPD4194	Approved
0.6901	Remote Similarity	NPD4192	Approved
0.6901	Remote Similarity	NPD4191	Approved
0.6901	Remote Similarity	NPD4193	Approved
0.6875	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5279	Phase 3
0.6824	Remote Similarity	NPD4519	Discontinued
0.6824	Remote Similarity	NPD4623	Approved
0.6824	Remote Similarity	NPD3618	Phase 1
0.6818	Remote Similarity	NPD6079	Approved
0.6747	Remote Similarity	NPD3667	Approved
0.6707	Remote Similarity	NPD7332	Phase 2
0.6707	Remote Similarity	NPD7514	Phase 3
0.6707	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD7145	Approved
0.6667	Remote Similarity	NPD4732	Discontinued
0.6667	Remote Similarity	NPD6110	Phase 1
0.6627	Remote Similarity	NPD6902	Approved
0.6625	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7144	Approved
0.6623	Remote Similarity	NPD7143	Approved
0.6591	Remote Similarity	NPD5328	Approved
0.6588	Remote Similarity	NPD4786	Approved
0.6588	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6925	Approved
0.6543	Remote Similarity	NPD5776	Phase 2
0.6538	Remote Similarity	NPD7152	Approved
0.6538	Remote Similarity	NPD7150	Approved
0.6538	Remote Similarity	NPD7151	Approved
0.6526	Remote Similarity	NPD5211	Phase 2
0.6522	Remote Similarity	NPD5221	Approved
0.6522	Remote Similarity	NPD5222	Approved
0.6522	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5785	Approved
0.6512	Remote Similarity	NPD5363	Approved
0.65	Remote Similarity	NPD6942	Approved
0.65	Remote Similarity	NPD7339	Approved
0.6494	Remote Similarity	NPD6923	Approved
0.6494	Remote Similarity	NPD6922	Approved
0.6479	Remote Similarity	NPD287	Approved
0.6452	Remote Similarity	NPD5173	Approved
0.6444	Remote Similarity	NPD7515	Phase 2
0.6437	Remote Similarity	NPD5690	Phase 2
0.6413	Remote Similarity	NPD5210	Approved
0.6413	Remote Similarity	NPD4629	Approved
0.6404	Remote Similarity	NPD4753	Phase 2
0.6392	Remote Similarity	NPD5141	Approved
0.6386	Remote Similarity	NPD6929	Approved
0.6386	Remote Similarity	NPD7645	Phase 2
0.6383	Remote Similarity	NPD5290	Discontinued
0.6383	Remote Similarity	NPD4225	Approved
0.6375	Remote Similarity	NPD6926	Approved
0.6375	Remote Similarity	NPD6924	Approved
0.6374	Remote Similarity	NPD4202	Approved
0.6364	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD4221	Approved
0.6353	Remote Similarity	NPD4223	Phase 3
0.6353	Remote Similarity	NPD5209	Approved
0.6341	Remote Similarity	NPD6932	Approved
0.6322	Remote Similarity	NPD1694	Approved
0.6316	Remote Similarity	NPD7331	Phase 2
0.6316	Remote Similarity	NPD4696	Approved
0.6316	Remote Similarity	NPD5286	Approved
0.6316	Remote Similarity	NPD5285	Approved
0.631	Remote Similarity	NPD4252	Approved
0.631	Remote Similarity	NPD6930	Phase 2
0.631	Remote Similarity	NPD6931	Approved
0.6301	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD4268	Approved
0.6265	Remote Similarity	NPD4271	Approved
0.6264	Remote Similarity	NPD7637	Suspended
0.625	Remote Similarity	NPD5223	Approved
0.6235	Remote Similarity	NPD6898	Phase 1
0.622	Remote Similarity	NPD6933	Approved
0.6207	Remote Similarity	NPD4197	Approved
0.6203	Remote Similarity	NPD4691	Approved
0.6186	Remote Similarity	NPD5224	Approved
0.6186	Remote Similarity	NPD5225	Approved
0.6186	Remote Similarity	NPD5226	Approved
0.6186	Remote Similarity	NPD4633	Approved
0.6184	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD4058	Approved
0.617	Remote Similarity	NPD4697	Phase 3
0.6163	Remote Similarity	NPD4270	Approved
0.6163	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD4269	Approved
0.6154	Remote Similarity	NPD4265	Approved
0.6146	Remote Similarity	NPD7639	Approved
0.6146	Remote Similarity	NPD7640	Approved
0.6136	Remote Similarity	NPD5329	Approved
0.6129	Remote Similarity	NPD7748	Approved
0.6122	Remote Similarity	NPD5175	Approved
0.6122	Remote Similarity	NPD5174	Approved
0.6118	Remote Similarity	NPD4820	Approved
0.6118	Remote Similarity	NPD4819	Approved
0.6118	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD4822	Approved
0.6118	Remote Similarity	NPD7525	Registered
0.6118	Remote Similarity	NPD4821	Approved
0.6105	Remote Similarity	NPD4755	Approved
0.6092	Remote Similarity	NPD6695	Phase 3
0.6092	Remote Similarity	NPD5332	Approved
0.6092	Remote Similarity	NPD5331	Approved
0.6092	Remote Similarity	NPD5362	Discontinued
0.6076	Remote Similarity	NPD4137	Phase 3
0.6071	Remote Similarity	NPD3617	Approved
0.6067	Remote Similarity	NPD6684	Approved
0.6067	Remote Similarity	NPD7146	Approved
0.6067	Remote Similarity	NPD4690	Approved
0.6067	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD5330	Approved
0.6067	Remote Similarity	NPD4689	Approved
0.6067	Remote Similarity	NPD4688	Approved
0.6067	Remote Similarity	NPD4694	Approved
0.6067	Remote Similarity	NPD7521	Approved
0.6067	Remote Similarity	NPD6409	Approved
0.6067	Remote Similarity	NPD4693	Phase 3
0.6067	Remote Similarity	NPD4138	Approved
0.6067	Remote Similarity	NPD7334	Approved
0.6067	Remote Similarity	NPD5205	Approved
0.6067	Remote Similarity	NPD5280	Approved
0.6064	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD4790	Discontinued
0.6042	Remote Similarity	NPD7638	Approved
0.6023	Remote Similarity	NPD3668	Phase 3
0.6023	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD5779	Approved
0.6022	Remote Similarity	NPD5778	Approved
0.6	Remote Similarity	NPD6683	Phase 2
0.6	Remote Similarity	NPD4747	Approved
0.5979	Remote Similarity	NPD4700	Approved
0.5976	Remote Similarity	NPD4687	Approved
0.5976	Remote Similarity	NPD4784	Approved
0.5976	Remote Similarity	NPD4785	Approved
0.5974	Remote Similarity	NPD7341	Phase 2
0.5955	Remote Similarity	NPD6893	Approved
0.5952	Remote Similarity	NPD4756	Discovery
0.5941	Remote Similarity	NPD5697	Approved
0.5938	Remote Similarity	NPD7902	Approved
0.5938	Remote Similarity	NPD6083	Phase 2
0.5938	Remote Similarity	NPD6084	Phase 2
0.5934	Remote Similarity	NPD4518	Approved
0.5934	Remote Similarity	NPD6903	Approved
0.5934	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.593	Remote Similarity	NPD7509	Discontinued
0.5926	Remote Similarity	NPD4243	Approved
0.5926	Remote Similarity	NPD5276	Approved
0.5921	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5344	Discontinued
0.5914	Remote Similarity	NPD5284	Approved
0.5914	Remote Similarity	NPD5281	Approved
0.5914	Remote Similarity	NPD6411	Approved
0.5909	Remote Similarity	NPD7154	Phase 3
0.5909	Remote Similarity	NPD4788	Approved
0.5904	Remote Similarity	NPD8039	Approved
0.5895	Remote Similarity	NPD5695	Phase 3
0.5889	Remote Similarity	NPD5786	Approved
0.5888	Remote Similarity	NPD7115	Discovery
0.5882	Remote Similarity	NPD6881	Approved
0.5882	Remote Similarity	NPD4730	Approved
0.5882	Remote Similarity	NPD6011	Approved
0.5882	Remote Similarity	NPD4729	Approved
0.5882	Remote Similarity	NPD6899	Approved
0.5882	Remote Similarity	NPD5168	Approved
0.5851	Remote Similarity	NPD6399	Phase 3
0.5825	Remote Similarity	NPD6013	Approved
0.5825	Remote Similarity	NPD6012	Approved
0.5825	Remote Similarity	NPD6014	Approved
0.5824	Remote Similarity	NPD3573	Approved
0.5824	Remote Similarity	NPD7524	Approved
0.5824	Remote Similarity	NPD7750	Discontinued
0.5806	Remote Similarity	NPD7136	Phase 2
0.5806	Remote Similarity	NPD7838	Discovery
0.5806	Remote Similarity	NPD4096	Approved
0.58	Remote Similarity	NPD4754	Approved
0.58	Remote Similarity	NPD6647	Phase 2
0.5789	Remote Similarity	NPD5282	Discontinued
0.5783	Remote Similarity	NPD5733	Approved
0.5769	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5250	Approved
0.5769	Remote Similarity	NPD5247	Approved
0.5769	Remote Similarity	NPD4634	Approved
0.5769	Remote Similarity	NPD5248	Approved
0.5769	Remote Similarity	NPD5251	Approved
0.5769	Remote Similarity	NPD7102	Approved
0.5769	Remote Similarity	NPD5249	Phase 3
0.5769	Remote Similarity	NPD6883	Approved
0.5769	Remote Similarity	NPD7290	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