NPASS Compound

Structure

NPC474862 OpenBabel07101718322D 25 25 0 0 1 0 0 0 0 0999 V2000 8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -2.5000 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 8 2 0 0 0 0 3 13 1 0 0 0 0 4 6 1 0 0 0 0 4 15 2 0 0 0 0 5 7 2 0 0 0 0 5 15 1 0 0 0 0 6 17 2 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 14 1 0 0 0 0 10 19 1 0 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 16 20 1 0 0 0 0 17 22 1 0 0 0 0 18 20 2 3 0 0 0 18 23 1 0 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	347.17
Volume:	365.116
LogP:	1.116
LogD:	0.901
LogS:	-1.689
# Rotatable Bonds:	10
TPSA:	106.86
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.404
Synthetic Accessibility Score:	3.033
Fsp3:	0.368
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:	-5.229
MDCK Permeability:	5.3846360970055684e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.223
Human Intestinal Absorption (HIA):	0.314
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.158

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.199
Plasma Protein Binding (PPB):	77.23284149169922%
Volume Distribution (VD):	0.26
Pgp-substrate:	36.47757339477539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.104
CYP1A2-substrate:	0.09
CYP2C19-inhibitor:	0.115
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.588
CYP2C9-substrate:	0.829
CYP2D6-inhibitor:	0.051
CYP2D6-substrate:	0.235
CYP3A4-inhibitor:	0.031
CYP3A4-substrate:	0.144

ADMET: Excretion

Clearance (CL):	2.546
Half-life (T1/2):	0.934

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.616
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.24
Skin Sensitization:	0.921
Carcinogencity:	0.141
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.01

Download Data

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

Natural Product: NPC474862

Natural Product ID:	NPC474862
*Common Name:**	Farinosone C
IUPAC Name:	(4E,6E)-8-[[1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl]amino]-3,5-dimethyl-8-oxoocta-4,6-dienoic acid
Synonyms:	farinosone C
Standard InCHIKey:	PWIPPVISROQJBU-FLUXNIISSA-N
Standard InCHI:	InChI=1S/C19H25NO5/c1-13(9-14(2)10-19(24)25)3-8-18(23)20-16(12-21)11-15-4-6-17(22)7-5-15/h3-9,14,16,21-22H,10-12H2,1-2H3,(H,20,23)(H,24,25)/b8-3+,13-9+
SMILES:	OCC(N=C(/C=C/C(=C/C(CC(=O)O)C)/C)O)Cc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485666
PubChem CID:	11336960
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000186] Phenethylamines [CHEMONTID:0000188] Amphetamines and derivatives

*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
NPO40482	Isaria farinosa	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568775]
NPO40482	Isaria farinosa	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921439]
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17067147]
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17988094]
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18284207]
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25600409]
NPO40482	Isaria farinosa	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33021377]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	27.0	%	PMID[491417]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	13.0	%	PMID[491417]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	47.0	%	PMID[491417]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	60.0	%	PMID[491417]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	53.0	%	PMID[491417]

☑ 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 NPC474862 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	99
0.1-0.2	668
0.2-0.3	3782
0.3-0.4	12309
0.4-0.5	9820
0.5-0.6	12241
0.6-0.7	3227
0.7-0.8	481
0.8-0.85	52
0.85-0.9	14
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.918	High Similarity	NPC296712
0.9068	High Similarity	NPC319950
0.88	High Similarity	NPC478147
0.8729	High Similarity	NPC317254
0.8689	High Similarity	NPC142577
0.8689	High Similarity	NPC27581
0.8682	High Similarity	NPC6570
0.8661	High Similarity	NPC45191
0.8661	High Similarity	NPC326966
0.864	High Similarity	NPC476353
0.8626	High Similarity	NPC197921
0.8561	High Similarity	NPC469360
0.8561	High Similarity	NPC91953
0.8522	High Similarity	NPC142297
0.8504	High Similarity	NPC325651
0.8487	Intermediate Similarity	NPC118202
0.8462	Intermediate Similarity	NPC474149
0.845	Intermediate Similarity	NPC328070
0.845	Intermediate Similarity	NPC244866
0.845	Intermediate Similarity	NPC470392
0.8443	Intermediate Similarity	NPC283760
0.8435	Intermediate Similarity	NPC231705
0.8376	Intermediate Similarity	NPC258056
0.8333	Intermediate Similarity	NPC473052
0.8333	Intermediate Similarity	NPC178902
0.8333	Intermediate Similarity	NPC473055
0.8291	Intermediate Similarity	NPC96224
0.8291	Intermediate Similarity	NPC24101
0.8279	Intermediate Similarity	NPC311737
0.8279	Intermediate Similarity	NPC38458
0.8271	Intermediate Similarity	NPC471201
0.8271	Intermediate Similarity	NPC322526
0.8258	Intermediate Similarity	NPC6913
0.8235	Intermediate Similarity	NPC81026
0.8197	Intermediate Similarity	NPC82963
0.8197	Intermediate Similarity	NPC281686
0.8197	Intermediate Similarity	NPC188867
0.8197	Intermediate Similarity	NPC106551
0.8162	Intermediate Similarity	NPC266741
0.8058	Intermediate Similarity	NPC132771
0.8	Intermediate Similarity	NPC239697
0.7983	Intermediate Similarity	NPC153690
0.7951	Intermediate Similarity	NPC309808
0.7937	Intermediate Similarity	NPC190663
0.7934	Intermediate Similarity	NPC227553
0.7934	Intermediate Similarity	NPC163674
0.7907	Intermediate Similarity	NPC62101
0.7907	Intermediate Similarity	NPC95733
0.7874	Intermediate Similarity	NPC56634
0.7868	Intermediate Similarity	NPC48202
0.7833	Intermediate Similarity	NPC31274
0.7832	Intermediate Similarity	NPC39431
0.7829	Intermediate Similarity	NPC307020
0.7812	Intermediate Similarity	NPC160493
0.7795	Intermediate Similarity	NPC80150
0.7787	Intermediate Similarity	NPC166837
0.7778	Intermediate Similarity	NPC122009
0.7778	Intermediate Similarity	NPC142638
0.7778	Intermediate Similarity	NPC317784
0.7769	Intermediate Similarity	NPC145638
0.7769	Intermediate Similarity	NPC290566
0.7769	Intermediate Similarity	NPC4974
0.7742	Intermediate Similarity	NPC142599
0.7734	Intermediate Similarity	NPC326079
0.7731	Intermediate Similarity	NPC211551
0.7721	Intermediate Similarity	NPC64205
0.7717	Intermediate Similarity	NPC268572
0.7717	Intermediate Similarity	NPC43275
0.771	Intermediate Similarity	NPC29477
0.7705	Intermediate Similarity	NPC63345
0.7698	Intermediate Similarity	NPC283468
0.7692	Intermediate Similarity	NPC211218
0.7692	Intermediate Similarity	NPC155847
0.7692	Intermediate Similarity	NPC289381
0.768	Intermediate Similarity	NPC10286
0.768	Intermediate Similarity	NPC213
0.7671	Intermediate Similarity	NPC212699
0.7671	Intermediate Similarity	NPC207675
0.7656	Intermediate Similarity	NPC263835
0.7639	Intermediate Similarity	NPC262166
0.763	Intermediate Similarity	NPC88667
0.7626	Intermediate Similarity	NPC168861
0.7623	Intermediate Similarity	NPC326187
0.7622	Intermediate Similarity	NPC473491
0.7607	Intermediate Similarity	NPC245561
0.7597	Intermediate Similarity	NPC473050
0.7597	Intermediate Similarity	NPC473051
0.7594	Intermediate Similarity	NPC16031
0.7594	Intermediate Similarity	NPC161593
0.7594	Intermediate Similarity	NPC145888
0.7556	Intermediate Similarity	NPC275538
0.7554	Intermediate Similarity	NPC476989
0.7551	Intermediate Similarity	NPC56635
0.7542	Intermediate Similarity	NPC52472
0.7541	Intermediate Similarity	NPC317305
0.754	Intermediate Similarity	NPC37302
0.7535	Intermediate Similarity	NPC16188
0.7521	Intermediate Similarity	NPC107619
0.7519	Intermediate Similarity	NPC476183
0.75	Intermediate Similarity	NPC314992
0.75	Intermediate Similarity	NPC474753
0.7482	Intermediate Similarity	NPC14600
0.7482	Intermediate Similarity	NPC41473
0.7482	Intermediate Similarity	NPC160607
0.7482	Intermediate Similarity	NPC214988
0.7482	Intermediate Similarity	NPC312770
0.7482	Intermediate Similarity	NPC204848
0.748	Intermediate Similarity	NPC2265
0.7478	Intermediate Similarity	NPC325292
0.7478	Intermediate Similarity	NPC138117
0.7463	Intermediate Similarity	NPC153990
0.7463	Intermediate Similarity	NPC251571
0.7463	Intermediate Similarity	NPC477839
0.7462	Intermediate Similarity	NPC476184
0.7462	Intermediate Similarity	NPC476281
0.746	Intermediate Similarity	NPC197513
0.7458	Intermediate Similarity	NPC125732
0.7458	Intermediate Similarity	NPC171843
0.7458	Intermediate Similarity	NPC12730
0.7456	Intermediate Similarity	NPC300017
0.745	Intermediate Similarity	NPC476194
0.744	Intermediate Similarity	NPC48525
0.7438	Intermediate Similarity	NPC13495
0.7434	Intermediate Similarity	NPC294516
0.7434	Intermediate Similarity	NPC107938
0.7426	Intermediate Similarity	NPC473724
0.7426	Intermediate Similarity	NPC257390
0.7422	Intermediate Similarity	NPC169328
0.7419	Intermediate Similarity	NPC183700
0.7417	Intermediate Similarity	NPC63931
0.7415	Intermediate Similarity	NPC476268
0.7415	Intermediate Similarity	NPC473580
0.7415	Intermediate Similarity	NPC244509
0.741	Intermediate Similarity	NPC313694
0.741	Intermediate Similarity	NPC242159
0.7395	Intermediate Similarity	NPC228400
0.7395	Intermediate Similarity	NPC214200
0.7391	Intermediate Similarity	NPC470441
0.7388	Intermediate Similarity	NPC210950
0.7388	Intermediate Similarity	NPC321561
0.7388	Intermediate Similarity	NPC199738
0.7385	Intermediate Similarity	NPC478015
0.7385	Intermediate Similarity	NPC478014
0.7385	Intermediate Similarity	NPC478016
0.7377	Intermediate Similarity	NPC327481
0.7376	Intermediate Similarity	NPC251439
0.7373	Intermediate Similarity	NPC260000
0.7372	Intermediate Similarity	NPC471953
0.7372	Intermediate Similarity	NPC214869
0.7368	Intermediate Similarity	NPC47667
0.7368	Intermediate Similarity	NPC280347
0.7368	Intermediate Similarity	NPC177420
0.7364	Intermediate Similarity	NPC237420
0.7364	Intermediate Similarity	NPC5932
0.7364	Intermediate Similarity	NPC310467
0.7361	Intermediate Similarity	NPC313414
0.736	Intermediate Similarity	NPC177576
0.7355	Intermediate Similarity	NPC88267
0.7355	Intermediate Similarity	NPC224610
0.7355	Intermediate Similarity	NPC194390
0.7355	Intermediate Similarity	NPC113326
0.7353	Intermediate Similarity	NPC52029
0.7353	Intermediate Similarity	NPC35961
0.7353	Intermediate Similarity	NPC195749
0.735	Intermediate Similarity	NPC3371
0.735	Intermediate Similarity	NPC313650
0.7348	Intermediate Similarity	NPC476278
0.7338	Intermediate Similarity	NPC475123
0.7338	Intermediate Similarity	NPC40234
0.7338	Intermediate Similarity	NPC475204
0.7338	Intermediate Similarity	NPC46009
0.7333	Intermediate Similarity	NPC40258
0.7333	Intermediate Similarity	NPC91461
0.7333	Intermediate Similarity	NPC7686
0.7333	Intermediate Similarity	NPC469243
0.7333	Intermediate Similarity	NPC318154
0.7329	Intermediate Similarity	NPC233702
0.7328	Intermediate Similarity	NPC284078
0.7328	Intermediate Similarity	NPC86966
0.732	Intermediate Similarity	NPC209463
0.7319	Intermediate Similarity	NPC169766
0.7319	Intermediate Similarity	NPC267237
0.7311	Intermediate Similarity	NPC51333
0.7311	Intermediate Similarity	NPC132078
0.7311	Intermediate Similarity	NPC280869
0.7311	Intermediate Similarity	NPC128723
0.7311	Intermediate Similarity	NPC216468
0.7311	Intermediate Similarity	NPC78119
0.7308	Intermediate Similarity	NPC158277
0.7308	Intermediate Similarity	NPC279871
0.7305	Intermediate Similarity	NPC299583
0.7305	Intermediate Similarity	NPC150712
0.7304	Intermediate Similarity	NPC55561
0.7302	Intermediate Similarity	NPC273814
0.7302	Intermediate Similarity	NPC474584
0.7302	Intermediate Similarity	NPC17693
0.7299	Intermediate Similarity	NPC114102
0.7299	Intermediate Similarity	NPC48909
0.7295	Intermediate Similarity	NPC303141
0.7295	Intermediate Similarity	NPC243677

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 NPC474862 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	96
0.1-0.2	395
0.2-0.3	922
0.3-0.4	2002
0.4-0.5	2787
0.5-0.6	2022
0.6-0.7	792
0.7-0.8	126
0.8-0.85	6
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9187	High Similarity	NPD3136	Phase 2
0.8889	High Similarity	NPD5729	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD7978	Discontinued
0.8211	Intermediate Similarity	NPD1759	Phase 1
0.8197	Intermediate Similarity	NPD9568	Approved
0.8134	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.813	Intermediate Similarity	NPD1758	Phase 1
0.7969	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD255	Approved
0.7967	Intermediate Similarity	NPD256	Approved
0.7842	Intermediate Similarity	NPD3400	Discontinued
0.784	Intermediate Similarity	NPD318	Approved
0.784	Intermediate Similarity	NPD317	Approved
0.7829	Intermediate Similarity	NPD4659	Approved
0.7797	Intermediate Similarity	NPD9608	Approved
0.7797	Intermediate Similarity	NPD9610	Approved
0.7786	Intermediate Similarity	NPD7451	Discontinued
0.7769	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD2562	Approved
0.7752	Intermediate Similarity	NPD2561	Approved
0.7698	Intermediate Similarity	NPD16	Approved
0.7698	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD856	Approved
0.7692	Intermediate Similarity	NPD6390	Discontinued
0.7681	Intermediate Similarity	NPD7450	Phase 2
0.7676	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD2229	Approved
0.7661	Intermediate Similarity	NPD2228	Approved
0.7661	Intermediate Similarity	NPD2234	Approved
0.7647	Intermediate Similarity	NPD555	Phase 2
0.7639	Intermediate Similarity	NPD7523	Phase 3
0.763	Intermediate Similarity	NPD259	Phase 1
0.7619	Intermediate Similarity	NPD7495	Discontinued
0.76	Intermediate Similarity	NPD9618	Approved
0.76	Intermediate Similarity	NPD9614	Approved
0.7597	Intermediate Similarity	NPD3421	Phase 3
0.7594	Intermediate Similarity	NPD9569	Approved
0.7576	Intermediate Similarity	NPD4103	Phase 2
0.7576	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6346	Approved
0.7569	Intermediate Similarity	NPD4186	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2218	Phase 2
0.75	Intermediate Similarity	NPD196	Phase 1
0.75	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2217	Approved
0.75	Intermediate Similarity	NPD5745	Approved
0.7481	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD3123	Discovery
0.7445	Intermediate Similarity	NPD825	Approved
0.7445	Intermediate Similarity	NPD826	Approved
0.7429	Intermediate Similarity	NPD9570	Approved
0.7424	Intermediate Similarity	NPD3685	Discontinued
0.741	Intermediate Similarity	NPD3553	Approved
0.741	Intermediate Similarity	NPD3552	Approved
0.741	Intermediate Similarity	NPD3554	Approved
0.741	Intermediate Similarity	NPD3555	Approved
0.7388	Intermediate Similarity	NPD258	Approved
0.7388	Intermediate Similarity	NPD257	Approved
0.7383	Intermediate Similarity	NPD8019	Approved
0.7377	Intermediate Similarity	NPD1445	Approved
0.7377	Intermediate Similarity	NPD1444	Approved
0.7364	Intermediate Similarity	NPD5304	Approved
0.7364	Intermediate Similarity	NPD5303	Approved
0.7353	Intermediate Similarity	NPD9536	Phase 1
0.7353	Intermediate Similarity	NPD5746	Approved
0.7353	Intermediate Similarity	NPD9537	Phase 1
0.7333	Intermediate Similarity	NPD854	Approved
0.7333	Intermediate Similarity	NPD855	Approved
0.7333	Intermediate Similarity	NPD7972	Discontinued
0.7315	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD1135	Approved
0.7313	Intermediate Similarity	NPD1129	Approved
0.7313	Intermediate Similarity	NPD1133	Approved
0.7313	Intermediate Similarity	NPD1134	Approved
0.7313	Intermediate Similarity	NPD1131	Approved
0.7293	Intermediate Similarity	NPD9622	Approved
0.7287	Intermediate Similarity	NPD9616	Approved
0.7287	Intermediate Similarity	NPD9613	Approved
0.7287	Intermediate Similarity	NPD9615	Approved
0.728	Intermediate Similarity	NPD3644	Approved
0.728	Intermediate Similarity	NPD3643	Approved
0.728	Intermediate Similarity	NPD3642	Approved
0.7273	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD2933	Approved
0.7265	Intermediate Similarity	NPD2934	Approved
0.726	Intermediate Similarity	NPD3536	Discontinued
0.7231	Intermediate Similarity	NPD316	Approved
0.7227	Intermediate Similarity	NPD9609	Approved
0.7227	Intermediate Similarity	NPD9611	Approved
0.7227	Intermediate Similarity	NPD9612	Approved
0.7218	Intermediate Similarity	NPD6624	Discontinued
0.7214	Intermediate Similarity	NPD2568	Approved
0.7203	Intermediate Similarity	NPD2859	Approved
0.7203	Intermediate Similarity	NPD2860	Approved
0.72	Intermediate Similarity	NPD1792	Phase 2
0.7197	Intermediate Similarity	NPD3847	Discontinued
0.7183	Intermediate Similarity	NPD2239	Approved
0.7183	Intermediate Similarity	NPD2240	Approved
0.7176	Intermediate Similarity	NPD4093	Discontinued
0.7174	Intermediate Similarity	NPD598	Approved
0.7174	Intermediate Similarity	NPD601	Approved
0.7174	Intermediate Similarity	NPD597	Approved
0.7174	Intermediate Similarity	NPD1048	Approved
0.7167	Intermediate Similarity	NPD3020	Approved
0.7167	Intermediate Similarity	NPD9712	Approved
0.7162	Intermediate Similarity	NPD7131	Phase 3
0.7154	Intermediate Similarity	NPD1040	Phase 2
0.7153	Intermediate Similarity	NPD2614	Approved
0.7143	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4739	Approved
0.7143	Intermediate Similarity	NPD8303	Discontinued
0.7133	Intermediate Similarity	NPD6502	Phase 2
0.7123	Intermediate Similarity	NPD6667	Approved
0.7123	Intermediate Similarity	NPD6666	Approved
0.7122	Intermediate Similarity	NPD1136	Approved
0.7122	Intermediate Similarity	NPD839	Approved
0.7122	Intermediate Similarity	NPD2674	Phase 3
0.7122	Intermediate Similarity	NPD1130	Approved
0.7122	Intermediate Similarity	NPD840	Approved
0.7122	Intermediate Similarity	NPD1132	Approved
0.7121	Intermediate Similarity	NPD9381	Approved
0.7121	Intermediate Similarity	NPD2668	Approved
0.7121	Intermediate Similarity	NPD9384	Approved
0.7121	Intermediate Similarity	NPD2667	Approved
0.7111	Intermediate Similarity	NPD3098	Discontinued
0.7101	Intermediate Similarity	NPD4738	Phase 2
0.7101	Intermediate Similarity	NPD9718	Approved
0.7099	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD3052	Approved
0.7092	Intermediate Similarity	NPD3054	Approved
0.7083	Intermediate Similarity	NPD9711	Approved
0.7083	Intermediate Similarity	NPD9710	Approved
0.7078	Intermediate Similarity	NPD2098	Approved
0.7073	Intermediate Similarity	NPD315	Approved
0.7073	Intermediate Similarity	NPD309	Approved
0.7073	Intermediate Similarity	NPD310	Approved
0.7073	Intermediate Similarity	NPD314	Approved
0.7073	Intermediate Similarity	NPD311	Approved
0.7073	Intermediate Similarity	NPD10	Approved
0.7071	Intermediate Similarity	NPD468	Phase 1
0.7067	Intermediate Similarity	NPD3455	Phase 2
0.7063	Intermediate Similarity	NPD1519	Approved
0.7063	Intermediate Similarity	NPD1538	Phase 1
0.7063	Intermediate Similarity	NPD1537	Approved
0.7059	Intermediate Similarity	NPD3053	Approved
0.7059	Intermediate Similarity	NPD3055	Approved
0.705	Intermediate Similarity	NPD3144	Approved
0.705	Intermediate Similarity	NPD3145	Approved
0.7045	Intermediate Similarity	NPD5981	Approved
0.7037	Intermediate Similarity	NPD1669	Approved
0.7031	Intermediate Similarity	NPD9379	Approved
0.7031	Intermediate Similarity	NPD9377	Approved
0.7031	Intermediate Similarity	NPD821	Approved
0.7021	Intermediate Similarity	NPD274	Approved
0.7021	Intermediate Similarity	NPD275	Approved
0.7014	Intermediate Similarity	NPD6809	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD7554	Discontinued
0.7007	Intermediate Similarity	NPD9619	Approved
0.7007	Intermediate Similarity	NPD9621	Approved
0.7007	Intermediate Similarity	NPD9620	Approved
0.7007	Intermediate Similarity	NPD602	Approved
0.7007	Intermediate Similarity	NPD599	Approved
0.7006	Intermediate Similarity	NPD7608	Discontinued
0.7	Intermediate Similarity	NPD829	Discontinued
0.7	Intermediate Similarity	NPD7477	Discontinued
0.7	Intermediate Similarity	NPD1348	Approved
0.7	Intermediate Similarity	NPD6405	Approved
0.7	Intermediate Similarity	NPD6407	Approved
0.6986	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD3125	Approved
0.698	Remote Similarity	NPD7303	Discontinued
0.6978	Remote Similarity	NPD5163	Phase 2
0.6975	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4479	Discontinued
0.6967	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3636	Approved
0.6957	Remote Similarity	NPD3637	Approved
0.6957	Remote Similarity	NPD3635	Approved
0.695	Remote Similarity	NPD2203	Discontinued
0.695	Remote Similarity	NPD3062	Approved
0.695	Remote Similarity	NPD3061	Approved
0.695	Remote Similarity	NPD3059	Approved
0.6948	Remote Similarity	NPD2097	Approved
0.6944	Remote Similarity	NPD1523	Approved
0.6944	Remote Similarity	NPD1522	Approved
0.6934	Remote Similarity	NPD2627	Approved
0.6934	Remote Similarity	NPD2628	Approved
0.6934	Remote Similarity	NPD2626	Approved
0.6934	Remote Similarity	NPD2159	Approved
0.6934	Remote Similarity	NPD2160	Approved
0.6934	Remote Similarity	NPD2625	Approved
0.693	Remote Similarity	NPD111	Approved
0.6929	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5356	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