NPASS Compound

Structure

NPC153660 OpenBabel07101718182D 21 21 0 0 1 0 0 0 0 0999 V2000 0.7412 2.7661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8267 1.4318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0793 5.1042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4773 -1.7812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9091 -0.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5852 3.2602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3381 2.3381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9102 3.9351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1691 1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2471 0.9220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6533 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8267 -1.4318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4161 2.0911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8267 0.4773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1573 4.8572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6533 -0.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4823 5.5321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4800 -1.4318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7573 -0.5811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 17 1 0 0 0 0 5 17 1 0 0 0 0 6 7 1 0 0 0 0 6 8 2 0 0 0 0 7 13 2 0 0 0 0 8 15 1 0 0 0 0 9 10 2 0 0 0 0 9 13 1 0 0 0 0 10 18 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 16 1 0 0 0 0 12 17 1 0 0 0 0 14 18 1 0 0 0 0 15 19 2 0 0 0 0 16 20 2 0 0 0 0 17 18 1 0 0 0 0 18 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.17
Volume:	321.88
LogP:	2.564
LogD:	2.06
LogS:	-2.794
# Rotatable Bonds:	4
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.638
Synthetic Accessibility Score:	3.925
Fsp3:	0.444
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.63
MDCK Permeability:	3.238724821130745e-05
Pgp-inhibitor:	0.472
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.243
Plasma Protein Binding (PPB):	84.31768035888672%
Volume Distribution (VD):	1.675
Pgp-substrate:	12.88168716430664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.215
CYP2C19-inhibitor:	0.185
CYP2C19-substrate:	0.799
CYP2C9-inhibitor:	0.207
CYP2C9-substrate:	0.09
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.118
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.862

ADMET: Excretion

Clearance (CL):	3.224
Half-life (T1/2):	0.812

ADMET: Toxicity

hERG Blockers:	0.086
Human Hepatotoxicity (H-HT):	0.838
Drug-inuced Liver Injury (DILI):	0.116
AMES Toxicity:	0.148
Rat Oral Acute Toxicity:	0.794
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.96
Carcinogencity:	0.892
Eye Corrosion:	0.004
Eye Irritation:	0.06
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: NPC153660

Natural Product ID:	NPC153660
*Common Name:**	(6S,7E,9E,11E)-3-Oxo-13-Apo-Alpha-Caroten-13-One
IUPAC Name:	(4S)-4-hydroxy-3,5,5-trimethyl-4-[(1E,3E,5E)-3-methyl-7-oxoocta-1,3,5-trienyl]cyclohex-2-en-1-one
Synonyms:
Standard InCHIKey:	MIYVERRWVRMENF-YPNYGIKRSA-N
Standard InCHI:	InChI=1S/C18H24O3/c1-13(7-6-8-15(3)19)9-10-18(21)14(2)11-16(20)12-17(18,4)5/h6-11,21H,12H2,1-5H3/b8-6+,10-9+,13-7+/t18-/m1/s1
SMILES:	C/C(=CC=CC(=O)C)/C=C/[C@]1(C(=CC(=O)CC1(C)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458039
PubChem CID:	11312272
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]
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]
NPO16333	Chenopodium album	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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	Activity	=	20.0	%	PMID[550244]

☑ 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 NPC153660 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	161
0.1-0.2	1272
0.2-0.3	7993
0.3-0.4	17389
0.4-0.5	9448
0.5-0.6	5032
0.6-0.7	1230
0.7-0.8	153
0.8-0.85	9
0.85-0.9	5
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9552	High Similarity	NPC136473
0.9155	High Similarity	NPC225665
0.9155	High Similarity	NPC169056
0.9155	High Similarity	NPC166018
0.8873	High Similarity	NPC201562
0.8873	High Similarity	NPC29542
0.8873	High Similarity	NPC323437
0.88	High Similarity	NPC160582
0.8219	Intermediate Similarity	NPC95863
0.8169	Intermediate Similarity	NPC269985
0.8169	Intermediate Similarity	NPC106613
0.8108	Intermediate Similarity	NPC186042
0.7949	Intermediate Similarity	NPC19900
0.7922	Intermediate Similarity	NPC82666
0.7821	Intermediate Similarity	NPC471409
0.7821	Intermediate Similarity	NPC475994
0.7821	Intermediate Similarity	NPC275494
0.7808	Intermediate Similarity	NPC117804
0.7794	Intermediate Similarity	NPC311852
0.7792	Intermediate Similarity	NPC7629
0.7792	Intermediate Similarity	NPC151622
0.7763	Intermediate Similarity	NPC122244
0.7763	Intermediate Similarity	NPC215050
0.7701	Intermediate Similarity	NPC78159
0.7692	Intermediate Similarity	NPC97173
0.7692	Intermediate Similarity	NPC34110
0.7662	Intermediate Similarity	NPC476346
0.7654	Intermediate Similarity	NPC158411
0.7654	Intermediate Similarity	NPC38796
0.7647	Intermediate Similarity	NPC474918
0.7632	Intermediate Similarity	NPC276336
0.7632	Intermediate Similarity	NPC247586
0.7606	Intermediate Similarity	NPC190049
0.76	Intermediate Similarity	NPC203819
0.7595	Intermediate Similarity	NPC189485
0.7531	Intermediate Similarity	NPC226068
0.7531	Intermediate Similarity	NPC6663
0.7529	Intermediate Similarity	NPC48107
0.7529	Intermediate Similarity	NPC72397
0.75	Intermediate Similarity	NPC170394
0.75	Intermediate Similarity	NPC150162
0.75	Intermediate Similarity	NPC27817
0.75	Intermediate Similarity	NPC472974
0.747	Intermediate Similarity	NPC476412
0.7468	Intermediate Similarity	NPC266193
0.7468	Intermediate Similarity	NPC257666
0.7468	Intermediate Similarity	NPC97377
0.7465	Intermediate Similarity	NPC64985
0.7442	Intermediate Similarity	NPC118011
0.7442	Intermediate Similarity	NPC36668
0.7442	Intermediate Similarity	NPC472676
0.7442	Intermediate Similarity	NPC472688
0.7439	Intermediate Similarity	NPC92226
0.7439	Intermediate Similarity	NPC469806
0.7439	Intermediate Similarity	NPC469799
0.7432	Intermediate Similarity	NPC254886
0.7412	Intermediate Similarity	NPC471792
0.7407	Intermediate Similarity	NPC476809
0.7407	Intermediate Similarity	NPC469637
0.7403	Intermediate Similarity	NPC180015
0.7403	Intermediate Similarity	NPC56747
0.7403	Intermediate Similarity	NPC109576
0.7403	Intermediate Similarity	NPC130016
0.7381	Intermediate Similarity	NPC476426
0.7375	Intermediate Similarity	NPC169095
0.7375	Intermediate Similarity	NPC62336
0.7361	Intermediate Similarity	NPC288253
0.7349	Intermediate Similarity	NPC3856
0.7349	Intermediate Similarity	NPC279639
0.7349	Intermediate Similarity	NPC49019
0.7342	Intermediate Similarity	NPC110725
0.7342	Intermediate Similarity	NPC472305
0.7342	Intermediate Similarity	NPC263582
0.7342	Intermediate Similarity	NPC76966
0.7342	Intermediate Similarity	NPC186554
0.7326	Intermediate Similarity	NPC58271
0.7326	Intermediate Similarity	NPC471791
0.7326	Intermediate Similarity	NPC471793
0.7317	Intermediate Similarity	NPC470298
0.7317	Intermediate Similarity	NPC225515
0.7313	Intermediate Similarity	NPC37644
0.7308	Intermediate Similarity	NPC213223
0.7303	Intermediate Similarity	NPC299100
0.7294	Intermediate Similarity	NPC194417
0.7284	Intermediate Similarity	NPC308038
0.7273	Intermediate Similarity	NPC204341
0.7273	Intermediate Similarity	NPC21944
0.7273	Intermediate Similarity	NPC133253
0.7273	Intermediate Similarity	NPC84790
0.7262	Intermediate Similarity	NPC87552
0.726	Intermediate Similarity	NPC4638
0.7241	Intermediate Similarity	NPC472973
0.7229	Intermediate Similarity	NPC279186
0.7229	Intermediate Similarity	NPC469805
0.7229	Intermediate Similarity	NPC469804
0.7222	Intermediate Similarity	NPC329416
0.7222	Intermediate Similarity	NPC317025
0.7222	Intermediate Similarity	NPC180950
0.7222	Intermediate Similarity	NPC317177
0.7222	Intermediate Similarity	NPC326645
0.7222	Intermediate Similarity	NPC269737
0.7209	Intermediate Similarity	NPC287079
0.7209	Intermediate Similarity	NPC476409
0.72	Intermediate Similarity	NPC278895
0.7195	Intermediate Similarity	NPC472301
0.7195	Intermediate Similarity	NPC45495
0.7195	Intermediate Similarity	NPC469798
0.7195	Intermediate Similarity	NPC469797
0.7195	Intermediate Similarity	NPC172013
0.7179	Intermediate Similarity	NPC12815
0.7179	Intermediate Similarity	NPC215745
0.7179	Intermediate Similarity	NPC238948
0.7176	Intermediate Similarity	NPC307112
0.7176	Intermediate Similarity	NPC70685
0.7174	Intermediate Similarity	NPC103051
0.7162	Intermediate Similarity	NPC251118
0.716	Intermediate Similarity	NPC179028
0.716	Intermediate Similarity	NPC248624
0.716	Intermediate Similarity	NPC231739
0.716	Intermediate Similarity	NPC198240
0.716	Intermediate Similarity	NPC74410
0.7143	Intermediate Similarity	NPC102197
0.7125	Intermediate Similarity	NPC250621
0.7125	Intermediate Similarity	NPC1254
0.7125	Intermediate Similarity	NPC180886
0.7125	Intermediate Similarity	NPC470525
0.7123	Intermediate Similarity	NPC322457
0.7108	Intermediate Similarity	NPC121984
0.7108	Intermediate Similarity	NPC473217
0.7108	Intermediate Similarity	NPC275766
0.7105	Intermediate Similarity	NPC310992
0.7105	Intermediate Similarity	NPC260474
0.7105	Intermediate Similarity	NPC87141
0.7105	Intermediate Similarity	NPC188292
0.7093	Intermediate Similarity	NPC183736
0.7093	Intermediate Similarity	NPC472985
0.7093	Intermediate Similarity	NPC239685
0.7093	Intermediate Similarity	NPC472986
0.7079	Intermediate Similarity	NPC472978
0.7079	Intermediate Similarity	NPC474018
0.7079	Intermediate Similarity	NPC473986
0.7079	Intermediate Similarity	NPC142838
0.7073	Intermediate Similarity	NPC474113
0.7073	Intermediate Similarity	NPC7232
0.7067	Intermediate Similarity	NPC308294
0.7067	Intermediate Similarity	NPC142423
0.7059	Intermediate Similarity	NPC14002
0.7059	Intermediate Similarity	NPC23117
0.7059	Intermediate Similarity	NPC251170
0.7051	Intermediate Similarity	NPC288667
0.7051	Intermediate Similarity	NPC144627
0.7045	Intermediate Similarity	NPC472983
0.7045	Intermediate Similarity	NPC262043
0.7037	Intermediate Similarity	NPC165711
0.7037	Intermediate Similarity	NPC471061
0.7037	Intermediate Similarity	NPC61952
0.7037	Intermediate Similarity	NPC203403
0.7037	Intermediate Similarity	NPC74995
0.7033	Intermediate Similarity	NPC476245
0.7027	Intermediate Similarity	NPC212210
0.7024	Intermediate Similarity	NPC472239
0.7024	Intermediate Similarity	NPC238991
0.7024	Intermediate Similarity	NPC3511
0.7024	Intermediate Similarity	NPC93590
0.7024	Intermediate Similarity	NPC302661
0.7024	Intermediate Similarity	NPC472867
0.7024	Intermediate Similarity	NPC142253
0.7015	Intermediate Similarity	NPC64866
0.7013	Intermediate Similarity	NPC256846
0.7013	Intermediate Similarity	NPC474060
0.7013	Intermediate Similarity	NPC469914
0.7011	Intermediate Similarity	NPC113370
0.7011	Intermediate Similarity	NPC136548
0.7011	Intermediate Similarity	NPC103743
0.7011	Intermediate Similarity	NPC476293
0.7011	Intermediate Similarity	NPC476079
0.7011	Intermediate Similarity	NPC181327
0.7	Intermediate Similarity	NPC251435
0.7	Intermediate Similarity	NPC131840
0.7	Intermediate Similarity	NPC325977
0.7	Intermediate Similarity	NPC134826
0.7	Intermediate Similarity	NPC476795
0.7	Intermediate Similarity	NPC114236
0.7	Intermediate Similarity	NPC476416
0.6988	Remote Similarity	NPC824
0.6988	Remote Similarity	NPC138492
0.6988	Remote Similarity	NPC74086
0.6988	Remote Similarity	NPC108955
0.6988	Remote Similarity	NPC233352
0.6988	Remote Similarity	NPC157895
0.6988	Remote Similarity	NPC148685
0.6988	Remote Similarity	NPC104120
0.6988	Remote Similarity	NPC471514
0.6986	Remote Similarity	NPC469728
0.6977	Remote Similarity	NPC474853
0.6977	Remote Similarity	NPC255174
0.6977	Remote Similarity	NPC179006
0.6977	Remote Similarity	NPC109528
0.6974	Remote Similarity	NPC263161
0.6966	Remote Similarity	NPC134321

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 NPC153660 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	1793
0.2-0.3	4210
0.3-0.4	2231
0.4-0.5	483
0.5-0.6	239
0.6-0.7	36
0.7-0.8	7
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
0.7294	Intermediate Similarity	NPD4623	Approved
0.7294	Intermediate Similarity	NPD4519	Discontinued
0.7222	Intermediate Similarity	NPD4191	Approved
0.7222	Intermediate Similarity	NPD4193	Approved
0.7222	Intermediate Similarity	NPD4194	Approved
0.7222	Intermediate Similarity	NPD4192	Approved
0.7176	Intermediate Similarity	NPD1696	Phase 3
0.7089	Intermediate Similarity	NPD4058	Approved
0.7067	Intermediate Similarity	NPD7331	Phase 2
0.6988	Remote Similarity	NPD4695	Discontinued
0.6988	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5280	Approved
0.6897	Remote Similarity	NPD4694	Approved
0.6897	Remote Similarity	NPD5690	Phase 2
0.6889	Remote Similarity	NPD5281	Approved
0.6889	Remote Similarity	NPD5284	Approved
0.6875	Remote Similarity	NPD4687	Approved
0.6835	Remote Similarity	NPD5276	Approved
0.6824	Remote Similarity	NPD4223	Phase 3
0.6824	Remote Similarity	NPD4221	Approved
0.6806	Remote Similarity	NPD287	Approved
0.6742	Remote Similarity	NPD4518	Approved
0.6709	Remote Similarity	NPD4691	Approved
0.6705	Remote Similarity	NPD3618	Phase 1
0.6705	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD5733	Approved
0.6667	Remote Similarity	NPD4195	Approved
0.6667	Remote Similarity	NPD4197	Approved
0.6627	Remote Similarity	NPD4756	Discovery
0.6593	Remote Similarity	NPD4096	Approved
0.6591	Remote Similarity	NPD5329	Approved
0.6585	Remote Similarity	NPD8264	Approved
0.6582	Remote Similarity	NPD4137	Phase 3
0.6528	Remote Similarity	NPD4219	Approved
0.6522	Remote Similarity	NPD6079	Approved
0.6517	Remote Similarity	NPD4688	Approved
0.6517	Remote Similarity	NPD4689	Approved
0.6517	Remote Similarity	NPD5205	Approved
0.6517	Remote Similarity	NPD4690	Approved
0.6517	Remote Similarity	NPD4138	Approved
0.6517	Remote Similarity	NPD4693	Phase 3
0.65	Remote Similarity	NPD4747	Approved
0.6494	Remote Similarity	NPD7341	Phase 2
0.6489	Remote Similarity	NPD5210	Approved
0.6489	Remote Similarity	NPD4629	Approved
0.6477	Remote Similarity	NPD3665	Phase 1
0.6477	Remote Similarity	NPD3133	Approved
0.6477	Remote Similarity	NPD3666	Approved
0.6447	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD3573	Approved
0.6429	Remote Similarity	NPD5211	Phase 2
0.6413	Remote Similarity	NPD5207	Approved
0.6386	Remote Similarity	NPD8039	Approved
0.6364	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD3617	Approved
0.6353	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD368	Approved
0.6304	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5328	Approved
0.6304	Remote Similarity	NPD4753	Phase 2
0.63	Remote Similarity	NPD5141	Approved
0.6277	Remote Similarity	NPD5133	Approved
0.6277	Remote Similarity	NPD4202	Approved
0.625	Remote Similarity	NPD5222	Approved
0.625	Remote Similarity	NPD5221	Approved
0.625	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5209	Approved
0.625	Remote Similarity	NPD3667	Approved
0.6237	Remote Similarity	NPD5785	Approved
0.6224	Remote Similarity	NPD5285	Approved
0.6224	Remote Similarity	NPD5286	Approved
0.6224	Remote Similarity	NPD6404	Discontinued
0.6224	Remote Similarity	NPD4696	Approved
0.6222	Remote Similarity	NPD1694	Approved
0.6222	Remote Similarity	NPD5363	Approved
0.6186	Remote Similarity	NPD5173	Approved
0.6184	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.618	Remote Similarity	NPD6110	Phase 1
0.617	Remote Similarity	NPD5694	Approved
0.617	Remote Similarity	NPD7515	Phase 2
0.6163	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD5223	Approved
0.6145	Remote Similarity	NPD4732	Discontinued
0.6111	Remote Similarity	NPD4786	Approved
0.61	Remote Similarity	NPD5091	Approved
0.61	Remote Similarity	NPD5225	Approved
0.61	Remote Similarity	NPD5226	Approved
0.61	Remote Similarity	NPD5224	Approved
0.61	Remote Similarity	NPD4633	Approved
0.6082	Remote Similarity	NPD4697	Phase 3
0.6067	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD5692	Phase 3
0.6049	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD7748	Approved
0.604	Remote Similarity	NPD5174	Approved
0.604	Remote Similarity	NPD5175	Approved
0.6023	Remote Similarity	NPD4252	Approved
0.6023	Remote Similarity	NPD7332	Phase 2
0.6023	Remote Similarity	NPD7514	Phase 3
0.602	Remote Similarity	NPD7902	Approved
0.602	Remote Similarity	NPD4755	Approved
0.6	Remote Similarity	NPD4220	Pre-registration
0.6	Remote Similarity	NPD6050	Approved
0.6	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD5695	Phase 3
0.5963	Remote Similarity	NPD7115	Discovery
0.596	Remote Similarity	NPD5696	Approved
0.596	Remote Similarity	NPD4225	Approved
0.5955	Remote Similarity	NPD4692	Approved
0.5955	Remote Similarity	NPD4139	Approved
0.5949	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5779	Approved
0.5938	Remote Similarity	NPD5778	Approved
0.59	Remote Similarity	NPD4700	Approved
0.5889	Remote Similarity	NPD4270	Approved
0.5889	Remote Similarity	NPD4269	Approved
0.5876	Remote Similarity	NPD6001	Approved
0.5876	Remote Similarity	NPD5282	Discontinued
0.5865	Remote Similarity	NPD5697	Approved
0.5859	Remote Similarity	NPD6084	Phase 2
0.5859	Remote Similarity	NPD6083	Phase 2
0.5851	Remote Similarity	NPD5208	Approved
0.5833	Remote Similarity	NPD6411	Approved
0.5833	Remote Similarity	NPD7637	Suspended
0.5833	Remote Similarity	NPD5693	Phase 1
0.5824	Remote Similarity	NPD4788	Approved
0.5816	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.581	Remote Similarity	NPD6011	Approved
0.581	Remote Similarity	NPD6881	Approved
0.581	Remote Similarity	NPD4730	Approved
0.581	Remote Similarity	NPD6899	Approved
0.581	Remote Similarity	NPD4729	Approved
0.5806	Remote Similarity	NPD7521	Approved
0.5806	Remote Similarity	NPD6409	Approved
0.5806	Remote Similarity	NPD7334	Approved
0.5806	Remote Similarity	NPD7146	Approved
0.5806	Remote Similarity	NPD6684	Approved
0.5806	Remote Similarity	NPD5330	Approved
0.5795	Remote Similarity	NPD7145	Approved
0.5794	Remote Similarity	NPD6649	Approved
0.5794	Remote Similarity	NPD6650	Approved
0.5789	Remote Similarity	NPD6673	Approved
0.5789	Remote Similarity	NPD6904	Approved
0.5789	Remote Similarity	NPD6080	Approved
0.5778	Remote Similarity	NPD8028	Phase 2
0.5778	Remote Similarity	NPD6902	Approved
0.5775	Remote Similarity	NPD3173	Approved
0.5773	Remote Similarity	NPD6399	Phase 3
0.5761	Remote Similarity	NPD3668	Phase 3
0.5761	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD7614	Phase 1
0.5755	Remote Similarity	NPD6014	Approved
0.5755	Remote Similarity	NPD6012	Approved
0.5755	Remote Similarity	NPD6013	Approved
0.5755	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD7639	Approved
0.5743	Remote Similarity	NPD7640	Approved
0.5733	Remote Similarity	NPD342	Phase 1
0.5733	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD4754	Approved
0.5714	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7900	Approved
0.5714	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7144	Approved
0.5714	Remote Similarity	NPD7143	Approved
0.5701	Remote Similarity	NPD6883	Approved
0.5701	Remote Similarity	NPD5135	Approved
0.5701	Remote Similarity	NPD5250	Approved
0.5701	Remote Similarity	NPD5251	Approved
0.5701	Remote Similarity	NPD5249	Phase 3
0.5701	Remote Similarity	NPD5248	Approved
0.5701	Remote Similarity	NPD7290	Approved
0.5701	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD4634	Approved
0.5701	Remote Similarity	NPD7102	Approved
0.5701	Remote Similarity	NPD5169	Approved
0.5701	Remote Similarity	NPD5247	Approved
0.5698	Remote Similarity	NPD6924	Approved
0.5698	Remote Similarity	NPD4785	Approved
0.5698	Remote Similarity	NPD4784	Approved
0.5698	Remote Similarity	NPD6926	Approved
0.5684	Remote Similarity	NPD6903	Approved
0.5684	Remote Similarity	NPD5737	Approved
0.5684	Remote Similarity	NPD6672	Approved
0.5684	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD5776	Phase 2
0.5682	Remote Similarity	NPD6932	Approved
0.5682	Remote Similarity	NPD6925	Approved
0.5676	Remote Similarity	NPD3172	Approved
0.5667	Remote Similarity	NPD4820	Approved
0.5667	Remote Similarity	NPD4822	Approved
0.5667	Remote Similarity	NPD4821	Approved
0.5667	Remote Similarity	NPD4819	Approved
0.5667	Remote Similarity	NPD6931	Approved
0.5667	Remote Similarity	NPD6930	Phase 2
0.566	Remote Similarity	NPD5128	Approved
0.566	Remote Similarity	NPD5168	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