NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	274.19
Volume:	315.726
LogP:	3.762
LogD:	2.384
LogS:	-3.349
# Rotatable Bonds:	4
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.478
Synthetic Accessibility Score:	4.091
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.653
MDCK Permeability:	2.9729490051977336e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.687
Human Intestinal Absorption (HIA):	0.094
20% Bioavailability (F20%):	0.638
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	90.99468231201172%
Volume Distribution (VD):	2.824
Pgp-substrate:	5.702980041503906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.119
CYP2C19-inhibitor:	0.071
CYP2C19-substrate:	0.855
CYP2C9-inhibitor:	0.139
CYP2C9-substrate:	0.283
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.651
CYP3A4-inhibitor:	0.037
CYP3A4-substrate:	0.612

ADMET: Excretion

Clearance (CL):	2.017
Half-life (T1/2):	0.694

ADMET: Toxicity

hERG Blockers:	0.174
Human Hepatotoxicity (H-HT):	0.657
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.531
Rat Oral Acute Toxicity:	0.8
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.914
Carcinogencity:	0.082
Eye Corrosion:	0.004
Eye Irritation:	0.261
Respiratory Toxicity:	0.94

Download Data

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

Natural Product: NPC95863

Natural Product ID:	NPC95863
*Common Name:**	(3R,6R,7E,9E,11E)-3-Hydroxy-13-Apo-Alpha-Caroten-13-One
IUPAC Name:	(3E,5E,7E)-8-[(1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-6-methylocta-3,5,7-trien-2-one
Synonyms:
Standard InCHIKey:	VFISUJDCZMSIKT-QNPHLTMISA-N
Standard InCHI:	InChI=1S/C18H26O2/c1-13(7-6-8-15(3)19)9-10-17-14(2)11-16(20)12-18(17,4)5/h6-11,16-17,20H,12H2,1-5H3/b8-6+,10-9+,13-7+/t16-,17-/m0/s1
SMILES:	C/C(=CC=CC(=O)C)/C=C/[C@H]1C(=C[C@@H](CC1(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458038
PubChem CID:	11403096
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[492489]

☑ 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 NPC95863 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	156
0.1-0.2	1104
0.2-0.3	6757
0.3-0.4	17335
0.4-0.5	9430
0.5-0.6	5877
0.6-0.7	1790
0.7-0.8	231
0.8-0.85	14
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC117804
0.8732	High Similarity	NPC186042
0.8553	High Similarity	NPC6663
0.84	Intermediate Similarity	NPC475994
0.8289	Intermediate Similarity	NPC19900
0.8286	Intermediate Similarity	NPC106613
0.8219	Intermediate Similarity	NPC201562
0.8219	Intermediate Similarity	NPC29542
0.8219	Intermediate Similarity	NPC323437
0.8219	Intermediate Similarity	NPC153660
0.8125	Intermediate Similarity	NPC109528
0.8108	Intermediate Similarity	NPC215050
0.8026	Intermediate Similarity	NPC203403
0.8	Intermediate Similarity	NPC69383
0.8	Intermediate Similarity	NPC171148
0.8	Intermediate Similarity	NPC313179
0.7975	Intermediate Similarity	NPC38796
0.7975	Intermediate Similarity	NPC158411
0.7975	Intermediate Similarity	NPC224455
0.7901	Intermediate Similarity	NPC476426
0.7895	Intermediate Similarity	NPC250621
0.7879	Intermediate Similarity	NPC48891
0.7875	Intermediate Similarity	NPC57370
0.7821	Intermediate Similarity	NPC308038
0.7808	Intermediate Similarity	NPC136473
0.7808	Intermediate Similarity	NPC471560
0.7805	Intermediate Similarity	NPC194417
0.7792	Intermediate Similarity	NPC149550
0.7792	Intermediate Similarity	NPC85105
0.7792	Intermediate Similarity	NPC476007
0.7778	Intermediate Similarity	NPC114651
0.7778	Intermediate Similarity	NPC302360
0.7778	Intermediate Similarity	NPC269985
0.7763	Intermediate Similarity	NPC474885
0.7733	Intermediate Similarity	NPC130665
0.7722	Intermediate Similarity	NPC471514
0.7711	Intermediate Similarity	NPC287079
0.7703	Intermediate Similarity	NPC286154
0.7703	Intermediate Similarity	NPC34834
0.7703	Intermediate Similarity	NPC203819
0.7692	Intermediate Similarity	NPC62336
0.7662	Intermediate Similarity	NPC263582
0.7654	Intermediate Similarity	NPC79945
0.7625	Intermediate Similarity	NPC6434
0.7619	Intermediate Similarity	NPC229612
0.7619	Intermediate Similarity	NPC7280
0.76	Intermediate Similarity	NPC67076
0.76	Intermediate Similarity	NPC319163
0.76	Intermediate Similarity	NPC474884
0.759	Intermediate Similarity	NPC472974
0.7571	Intermediate Similarity	NPC269737
0.7564	Intermediate Similarity	NPC74995
0.7561	Intermediate Similarity	NPC476412
0.7532	Intermediate Similarity	NPC114236
0.7532	Intermediate Similarity	NPC169056
0.7532	Intermediate Similarity	NPC166018
0.7532	Intermediate Similarity	NPC225665
0.7531	Intermediate Similarity	NPC93590
0.75	Intermediate Similarity	NPC45495
0.75	Intermediate Similarity	NPC71755
0.75	Intermediate Similarity	NPC160582
0.75	Intermediate Similarity	NPC281880
0.747	Intermediate Similarity	NPC179006
0.747	Intermediate Similarity	NPC474853
0.7442	Intermediate Similarity	NPC182136
0.7442	Intermediate Similarity	NPC19771
0.7436	Intermediate Similarity	NPC470525
0.7436	Intermediate Similarity	NPC253190
0.7432	Intermediate Similarity	NPC471238
0.7424	Intermediate Similarity	NPC14002
0.7412	Intermediate Similarity	NPC60765
0.7407	Intermediate Similarity	NPC159148
0.7407	Intermediate Similarity	NPC121984
0.7403	Intermediate Similarity	NPC227814
0.7403	Intermediate Similarity	NPC144995
0.7386	Intermediate Similarity	NPC299100
0.7381	Intermediate Similarity	NPC472986
0.7381	Intermediate Similarity	NPC472985
0.7375	Intermediate Similarity	NPC170394
0.7375	Intermediate Similarity	NPC152061
0.7375	Intermediate Similarity	NPC7232
0.7361	Intermediate Similarity	NPC107540
0.7361	Intermediate Similarity	NPC290367
0.7356	Intermediate Similarity	NPC212948
0.7353	Intermediate Similarity	NPC55412
0.7353	Intermediate Similarity	NPC249645
0.7349	Intermediate Similarity	NPC33913
0.7342	Intermediate Similarity	NPC91594
0.7342	Intermediate Similarity	NPC86917
0.7342	Intermediate Similarity	NPC470428
0.7342	Intermediate Similarity	NPC82666
0.7342	Intermediate Similarity	NPC471061
0.7333	Intermediate Similarity	NPC473893
0.7333	Intermediate Similarity	NPC474248
0.7326	Intermediate Similarity	NPC472973
0.7326	Intermediate Similarity	NPC472983
0.7326	Intermediate Similarity	NPC210216
0.7326	Intermediate Similarity	NPC123912
0.7326	Intermediate Similarity	NPC257485
0.7324	Intermediate Similarity	NPC317177
0.7324	Intermediate Similarity	NPC326645
0.7324	Intermediate Similarity	NPC329416
0.7324	Intermediate Similarity	NPC321867
0.7324	Intermediate Similarity	NPC68679
0.7324	Intermediate Similarity	NPC207007
0.7324	Intermediate Similarity	NPC317025
0.7317	Intermediate Similarity	NPC279186
0.7313	Intermediate Similarity	NPC5626
0.7303	Intermediate Similarity	NPC180950
0.7297	Intermediate Similarity	NPC254886
0.7297	Intermediate Similarity	NPC96962
0.7297	Intermediate Similarity	NPC69649
0.7297	Intermediate Similarity	NPC68703
0.7294	Intermediate Similarity	NPC136548
0.7286	Intermediate Similarity	NPC475931
0.7284	Intermediate Similarity	NPC271104
0.7284	Intermediate Similarity	NPC104120
0.7284	Intermediate Similarity	NPC148685
0.7284	Intermediate Similarity	NPC172013
0.7284	Intermediate Similarity	NPC157895
0.7273	Intermediate Similarity	NPC68443
0.7273	Intermediate Similarity	NPC214697
0.7273	Intermediate Similarity	NPC474736
0.7273	Intermediate Similarity	NPC276336
0.7262	Intermediate Similarity	NPC15807
0.726	Intermediate Similarity	NPC308844
0.7253	Intermediate Similarity	NPC103051
0.725	Intermediate Similarity	NPC478122
0.725	Intermediate Similarity	NPC471409
0.725	Intermediate Similarity	NPC172066
0.725	Intermediate Similarity	NPC297996
0.725	Intermediate Similarity	NPC476949
0.725	Intermediate Similarity	NPC275494
0.725	Intermediate Similarity	NPC167891
0.725	Intermediate Similarity	NPC83351
0.725	Intermediate Similarity	NPC189485
0.7246	Intermediate Similarity	NPC268185
0.7241	Intermediate Similarity	NPC310479
0.7229	Intermediate Similarity	NPC470384
0.7229	Intermediate Similarity	NPC472377
0.7229	Intermediate Similarity	NPC311070
0.7229	Intermediate Similarity	NPC105173
0.7222	Intermediate Similarity	NPC301534
0.7222	Intermediate Similarity	NPC250757
0.7215	Intermediate Similarity	NPC469646
0.7215	Intermediate Similarity	NPC265588
0.7209	Intermediate Similarity	NPC474854
0.7206	Intermediate Similarity	NPC232247
0.7206	Intermediate Similarity	NPC317899
0.7206	Intermediate Similarity	NPC251666
0.72	Intermediate Similarity	NPC96484
0.7195	Intermediate Similarity	NPC136150
0.7195	Intermediate Similarity	NPC116797
0.7195	Intermediate Similarity	NPC470298
0.7191	Intermediate Similarity	NPC469491
0.7191	Intermediate Similarity	NPC473162
0.7191	Intermediate Similarity	NPC78159
0.7191	Intermediate Similarity	NPC474690
0.7183	Intermediate Similarity	NPC66020
0.7179	Intermediate Similarity	NPC78527
0.7179	Intermediate Similarity	NPC306727
0.7176	Intermediate Similarity	NPC183736
0.7164	Intermediate Similarity	NPC23117
0.7162	Intermediate Similarity	NPC255781
0.7162	Intermediate Similarity	NPC137163
0.7162	Intermediate Similarity	NPC202017
0.7162	Intermediate Similarity	NPC149680
0.7162	Intermediate Similarity	NPC267027
0.716	Intermediate Similarity	NPC281138
0.716	Intermediate Similarity	NPC474113
0.716	Intermediate Similarity	NPC470429
0.716	Intermediate Similarity	NPC242767
0.7159	Intermediate Similarity	NPC475806
0.7159	Intermediate Similarity	NPC472978
0.7143	Intermediate Similarity	NPC471268
0.7143	Intermediate Similarity	NPC230527
0.7143	Intermediate Similarity	NPC477792
0.7143	Intermediate Similarity	NPC53385
0.7143	Intermediate Similarity	NPC471271
0.7143	Intermediate Similarity	NPC181872
0.7143	Intermediate Similarity	NPC311852
0.7143	Intermediate Similarity	NPC231310
0.7143	Intermediate Similarity	NPC155025
0.7143	Intermediate Similarity	NPC472265
0.7143	Intermediate Similarity	NPC316185
0.7143	Intermediate Similarity	NPC99726
0.7143	Intermediate Similarity	NPC7927
0.7143	Intermediate Similarity	NPC238485
0.7143	Intermediate Similarity	NPC471272
0.7143	Intermediate Similarity	NPC226848
0.7143	Intermediate Similarity	NPC242001
0.7126	Intermediate Similarity	NPC472240
0.7126	Intermediate Similarity	NPC146554
0.7126	Intermediate Similarity	NPC473999
0.7126	Intermediate Similarity	NPC36668
0.7126	Intermediate Similarity	NPC314727
0.7126	Intermediate Similarity	NPC118011
0.7126	Intermediate Similarity	NPC262858
0.7126	Intermediate Similarity	NPC309603
0.7125	Intermediate Similarity	NPC97377

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 NPC95863 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	1597
0.2-0.3	4275
0.3-0.4	2313
0.4-0.5	519
0.5-0.6	230
0.6-0.7	65
0.7-0.8	10
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
0.8	Intermediate Similarity	NPD8264	Approved
0.7353	Intermediate Similarity	NPD4219	Approved
0.7324	Intermediate Similarity	NPD4192	Approved
0.7324	Intermediate Similarity	NPD4193	Approved
0.7324	Intermediate Similarity	NPD4191	Approved
0.7324	Intermediate Similarity	NPD368	Approved
0.7324	Intermediate Similarity	NPD4194	Approved
0.7262	Intermediate Similarity	NPD1696	Phase 3
0.725	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5279	Phase 3
0.7073	Intermediate Similarity	NPD7514	Phase 3
0.7073	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7332	Phase 2
0.7051	Intermediate Similarity	NPD4732	Discontinued
0.7037	Intermediate Similarity	NPD7145	Approved
0.7013	Intermediate Similarity	NPD7144	Approved
0.7013	Intermediate Similarity	NPD7143	Approved
0.6988	Remote Similarity	NPD6902	Approved
0.6957	Remote Similarity	NPD342	Phase 1
0.6951	Remote Similarity	NPD4195	Approved
0.6941	Remote Similarity	NPD3666	Approved
0.6941	Remote Similarity	NPD3133	Approved
0.6941	Remote Similarity	NPD3665	Phase 1
0.6923	Remote Similarity	NPD7151	Approved
0.6923	Remote Similarity	NPD7152	Approved
0.6923	Remote Similarity	NPD7150	Approved
0.6914	Remote Similarity	NPD6925	Approved
0.6914	Remote Similarity	NPD5776	Phase 2
0.6883	Remote Similarity	NPD6922	Approved
0.6883	Remote Similarity	NPD6923	Approved
0.6829	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4623	Approved
0.6782	Remote Similarity	NPD4519	Discontinued
0.6782	Remote Similarity	NPD3618	Phase 1
0.6778	Remote Similarity	NPD6079	Approved
0.675	Remote Similarity	NPD6924	Approved
0.675	Remote Similarity	NPD6926	Approved
0.6747	Remote Similarity	NPD6929	Approved
0.6712	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6932	Approved
0.6706	Remote Similarity	NPD5209	Approved
0.6706	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD6931	Approved
0.6667	Remote Similarity	NPD6930	Phase 2
0.6667	Remote Similarity	NPD4695	Discontinued
0.6628	Remote Similarity	NPD6110	Phase 1
0.6593	Remote Similarity	NPD7637	Suspended
0.6588	Remote Similarity	NPD6898	Phase 1
0.6585	Remote Similarity	NPD6933	Approved
0.6585	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5328	Approved
0.6552	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4786	Approved
0.6543	Remote Similarity	NPD4058	Approved
0.6495	Remote Similarity	NPD5211	Phase 2
0.6489	Remote Similarity	NPD5222	Approved
0.6489	Remote Similarity	NPD5221	Approved
0.6489	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5785	Approved
0.6477	Remote Similarity	NPD5363	Approved
0.6463	Remote Similarity	NPD6942	Approved
0.6463	Remote Similarity	NPD7339	Approved
0.6447	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD6695	Phase 3
0.6421	Remote Similarity	NPD5173	Approved
0.6413	Remote Similarity	NPD7515	Phase 2
0.6404	Remote Similarity	NPD5280	Approved
0.6404	Remote Similarity	NPD5690	Phase 2
0.6404	Remote Similarity	NPD4694	Approved
0.6383	Remote Similarity	NPD5210	Approved
0.6383	Remote Similarity	NPD4629	Approved
0.6374	Remote Similarity	NPD4753	Phase 2
0.6364	Remote Similarity	NPD5141	Approved
0.6364	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4225	Approved
0.6354	Remote Similarity	NPD5290	Discontinued
0.6353	Remote Similarity	NPD7645	Phase 2
0.6353	Remote Similarity	NPD6683	Phase 2
0.6344	Remote Similarity	NPD5778	Approved
0.6344	Remote Similarity	NPD5779	Approved
0.6344	Remote Similarity	NPD4202	Approved
0.6341	Remote Similarity	NPD4687	Approved
0.6333	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD4221	Approved
0.6322	Remote Similarity	NPD4223	Phase 3
0.631	Remote Similarity	NPD4756	Discovery
0.6296	Remote Similarity	NPD5276	Approved
0.6292	Remote Similarity	NPD6893	Approved
0.6289	Remote Similarity	NPD5286	Approved
0.6289	Remote Similarity	NPD4696	Approved
0.6289	Remote Similarity	NPD5285	Approved
0.6282	Remote Similarity	NPD7331	Phase 2
0.6279	Remote Similarity	NPD4252	Approved
0.6279	Remote Similarity	NPD7509	Discontinued
0.6265	Remote Similarity	NPD8039	Approved
0.6264	Remote Similarity	NPD4518	Approved
0.6237	Remote Similarity	NPD5284	Approved
0.6237	Remote Similarity	NPD6411	Approved
0.6237	Remote Similarity	NPD5281	Approved
0.6235	Remote Similarity	NPD4271	Approved
0.6235	Remote Similarity	NPD4268	Approved
0.6224	Remote Similarity	NPD5223	Approved
0.6216	Remote Similarity	NPD287	Approved
0.618	Remote Similarity	NPD4197	Approved
0.6173	Remote Similarity	NPD4691	Approved
0.6162	Remote Similarity	NPD5226	Approved
0.6162	Remote Similarity	NPD4633	Approved
0.6162	Remote Similarity	NPD5225	Approved
0.6162	Remote Similarity	NPD5224	Approved
0.6154	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7524	Approved
0.6154	Remote Similarity	NPD7750	Discontinued
0.6146	Remote Similarity	NPD4697	Phase 3
0.6145	Remote Similarity	NPD5733	Approved
0.6136	Remote Similarity	NPD4270	Approved
0.6136	Remote Similarity	NPD4269	Approved
0.6136	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD4096	Approved
0.6129	Remote Similarity	NPD7838	Discovery
0.6129	Remote Similarity	NPD7136	Phase 2
0.6122	Remote Similarity	NPD7640	Approved
0.6122	Remote Similarity	NPD7639	Approved
0.6119	Remote Similarity	NPD4265	Approved
0.6111	Remote Similarity	NPD1694	Approved
0.6111	Remote Similarity	NPD5329	Approved
0.6105	Remote Similarity	NPD7748	Approved
0.61	Remote Similarity	NPD6647	Phase 2
0.61	Remote Similarity	NPD5174	Approved
0.61	Remote Similarity	NPD5175	Approved
0.6092	Remote Similarity	NPD7525	Registered
0.6092	Remote Similarity	NPD4820	Approved
0.6092	Remote Similarity	NPD4822	Approved
0.6092	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD4819	Approved
0.6092	Remote Similarity	NPD4821	Approved
0.6087	Remote Similarity	NPD4220	Pre-registration
0.6082	Remote Similarity	NPD4755	Approved
0.6067	Remote Similarity	NPD5331	Approved
0.6067	Remote Similarity	NPD5332	Approved
0.6067	Remote Similarity	NPD5362	Discontinued
0.6049	Remote Similarity	NPD4137	Phase 3
0.6047	Remote Similarity	NPD3617	Approved
0.6044	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD7334	Approved
0.6044	Remote Similarity	NPD6409	Approved
0.6044	Remote Similarity	NPD4693	Phase 3
0.6044	Remote Similarity	NPD7146	Approved
0.6044	Remote Similarity	NPD5205	Approved
0.6044	Remote Similarity	NPD4138	Approved
0.6044	Remote Similarity	NPD6684	Approved
0.6044	Remote Similarity	NPD4688	Approved
0.6044	Remote Similarity	NPD4689	Approved
0.6044	Remote Similarity	NPD5330	Approved
0.6044	Remote Similarity	NPD7521	Approved
0.6044	Remote Similarity	NPD4690	Approved
0.6023	Remote Similarity	NPD4790	Discontinued
0.6022	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD6101	Approved
0.6022	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.602	Remote Similarity	NPD7638	Approved
0.602	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3668	Phase 3
0.6	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD4747	Approved
0.596	Remote Similarity	NPD4700	Approved
0.596	Remote Similarity	NPD6404	Discontinued
0.596	Remote Similarity	NPD6648	Approved
0.5952	Remote Similarity	NPD4785	Approved
0.5952	Remote Similarity	NPD4784	Approved
0.5949	Remote Similarity	NPD7341	Phase 2
0.5922	Remote Similarity	NPD5697	Approved
0.5918	Remote Similarity	NPD6084	Phase 2
0.5918	Remote Similarity	NPD6083	Phase 2
0.5918	Remote Similarity	NPD7902	Approved
0.5914	Remote Similarity	NPD6903	Approved
0.5914	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD4243	Approved
0.59	Remote Similarity	NPD5344	Discontinued
0.5897	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD7087	Discontinued
0.5889	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD7154	Phase 3
0.5889	Remote Similarity	NPD4788	Approved
0.5876	Remote Similarity	NPD5695	Phase 3
0.5876	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD7115	Discovery
0.587	Remote Similarity	NPD5786	Approved
0.5865	Remote Similarity	NPD6899	Approved
0.5865	Remote Similarity	NPD5168	Approved
0.5865	Remote Similarity	NPD6011	Approved
0.5865	Remote Similarity	NPD4730	Approved
0.5865	Remote Similarity	NPD4729	Approved
0.5865	Remote Similarity	NPD6881	Approved
0.5833	Remote Similarity	NPD5133	Approved
0.5833	Remote Similarity	NPD6399	Phase 3
0.581	Remote Similarity	NPD6012	Approved
0.581	Remote Similarity	NPD6014	Approved
0.581	Remote Similarity	NPD6013	Approved
0.5806	Remote Similarity	NPD3573	Approved
0.5789	Remote Similarity	NPD5207	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