NPASS Compound

Structure

CID180388 OpenBabel06191715552D 26 27 0 0 1 0 0 0 0 0999 V2000 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 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 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 10 1 0 0 0 0 4 12 1 0 0 0 0 5 25 1 0 0 0 0 6 10 2 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 14 1 0 0 0 0 9 26 1 0 0 0 0 10 20 1 0 0 0 0 11 3 1 1 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 12 21 2 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 17 2 0 0 0 0 15 22 1 1 0 0 0 17 18 1 0 0 0 0 18 19 2 0 0 0 0 18 23 1 0 0 0 0 19 25 1 0 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.16
Volume:	371.649
LogP:	2.869
LogD:	2.107
LogS:	-3.046
# Rotatable Bonds:	6
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.557
Synthetic Accessibility Score:	3.515
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.875
MDCK Permeability:	1.5212361176963896e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.103
Plasma Protein Binding (PPB):	94.59895324707031%
Volume Distribution (VD):	0.767
Pgp-substrate:	9.034636497497559%

ADMET: Metabolism

CYP1A2-inhibitor:	0.832
CYP1A2-substrate:	0.947
CYP2C19-inhibitor:	0.498
CYP2C19-substrate:	0.648
CYP2C9-inhibitor:	0.632
CYP2C9-substrate:	0.842
CYP2D6-inhibitor:	0.804
CYP2D6-substrate:	0.255
CYP3A4-inhibitor:	0.287
CYP3A4-substrate:	0.316

ADMET: Excretion

Clearance (CL):	7.803
Half-life (T1/2):	0.896

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.079
Drug-inuced Liver Injury (DILI):	0.222
AMES Toxicity:	0.452
Rat Oral Acute Toxicity:	0.42
Maximum Recommended Daily Dose:	0.356
Skin Sensitization:	0.407
Carcinogencity:	0.157
Eye Corrosion:	0.004
Eye Irritation:	0.853
Respiratory Toxicity:	0.251

Download Data

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

Natural Product: NPC180388

Natural Product ID:	NPC180388
*Common Name:**	14-Angeloyloxy-3Beta-Hydroxydeltonorcacalol
IUPAC Name:	[(7S,8R)-2-acetyl-3,7-dihydroxy-4-methoxy-8-methyl-7,8-dihydronaphthalen-1-yl]methyl (Z)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	RCIOEOWZSQVXEU-YKMVYGBISA-N
Standard InCHI:	InChI=1S/C20H24O6/c1-6-10(2)20(24)26-9-14-16-11(3)15(22)8-7-13(16)19(25-5)18(23)17(14)12(4)21/h6-8,11,15,22-23H,9H2,1-5H3/b10-6-/t11-,15-/m0/s1
SMILES:	C/C=C(/C)C(=O)OCc1c2[C@@H](C)[C@H](C=Cc2c(c(c1C(=O)C)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1641930
PubChem CID:	50901251
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0002441] Naphthols 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
NPO29766	Parasenecio deltophyllus	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[20968296]
NPO40261	Parasenecio hastatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31994874]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	200000.0	nM	PMID[495026]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	200000.0	nM	PMID[495026]

☑ 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 NPC180388 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	347
0.1-0.2	1337
0.2-0.3	3127
0.3-0.4	7069
0.4-0.5	11078
0.5-0.6	4556
0.6-0.7	6277
0.7-0.8	8021
0.8-0.85	821
0.85-0.9	59
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9862	High Similarity	NPC31132
0.947	High Similarity	NPC302258
0.8792	High Similarity	NPC11314
0.8718	High Similarity	NPC82592
0.8718	High Similarity	NPC16286
0.8718	High Similarity	NPC16082
0.8688	High Similarity	NPC477689
0.8684	High Similarity	NPC32058
0.8684	High Similarity	NPC85734
0.8675	High Similarity	NPC89664
0.8675	High Similarity	NPC274085
0.8662	High Similarity	NPC197751
0.8654	High Similarity	NPC281477
0.8654	High Similarity	NPC62051
0.8645	High Similarity	NPC473201
0.8645	High Similarity	NPC75377
0.8645	High Similarity	NPC302783
0.8642	High Similarity	NPC283041
0.8636	High Similarity	NPC303989
0.8634	High Similarity	NPC191930
0.8634	High Similarity	NPC474301
0.8625	High Similarity	NPC144843
0.8608	High Similarity	NPC190020
0.8608	High Similarity	NPC77679
0.8608	High Similarity	NPC84935
0.8608	High Similarity	NPC143328
0.8599	High Similarity	NPC79998
0.859	High Similarity	NPC295646
0.859	High Similarity	NPC3744
0.859	High Similarity	NPC137125
0.858	High Similarity	NPC263212
0.858	High Similarity	NPC20237
0.8571	High Similarity	NPC55327
0.8571	High Similarity	NPC249181
0.8562	High Similarity	NPC117985
0.8562	High Similarity	NPC474779
0.8553	High Similarity	NPC470339
0.8553	High Similarity	NPC477410
0.8553	High Similarity	NPC103910
0.8544	High Similarity	NPC478223
0.8544	High Similarity	NPC150227
0.8535	High Similarity	NPC474000
0.8528	High Similarity	NPC469521
0.8526	High Similarity	NPC70320
0.8526	High Similarity	NPC124842
0.8526	High Similarity	NPC144283
0.8509	High Similarity	NPC474763
0.8506	High Similarity	NPC8817
0.8506	High Similarity	NPC137296
0.85	High Similarity	NPC47623
0.85	High Similarity	NPC472961
0.85	High Similarity	NPC472055
0.85	High Similarity	NPC472962
0.8491	Intermediate Similarity	NPC167098
0.8491	Intermediate Similarity	NPC296044
0.8487	Intermediate Similarity	NPC46161
0.8487	Intermediate Similarity	NPC258307
0.8487	Intermediate Similarity	NPC239608
0.8481	Intermediate Similarity	NPC199926
0.8477	Intermediate Similarity	NPC84273
0.8471	Intermediate Similarity	NPC199773
0.8471	Intermediate Similarity	NPC164912
0.8466	Intermediate Similarity	NPC329119
0.8457	Intermediate Similarity	NPC317781
0.8457	Intermediate Similarity	NPC475055
0.8447	Intermediate Similarity	NPC318081
0.8447	Intermediate Similarity	NPC473106
0.8447	Intermediate Similarity	NPC103201
0.8443	Intermediate Similarity	NPC475054
0.8442	Intermediate Similarity	NPC58752
0.8442	Intermediate Similarity	NPC470357
0.8438	Intermediate Similarity	NPC315157
0.8438	Intermediate Similarity	NPC45846
0.8434	Intermediate Similarity	NPC199357
0.8431	Intermediate Similarity	NPC469683
0.8428	Intermediate Similarity	NPC472050
0.8428	Intermediate Similarity	NPC279605
0.8428	Intermediate Similarity	NPC227062
0.8421	Intermediate Similarity	NPC314271
0.8415	Intermediate Similarity	NPC473094
0.8411	Intermediate Similarity	NPC220496
0.8411	Intermediate Similarity	NPC147542
0.8411	Intermediate Similarity	NPC37992
0.8411	Intermediate Similarity	NPC241349
0.8411	Intermediate Similarity	NPC327916
0.8411	Intermediate Similarity	NPC42262
0.8411	Intermediate Similarity	NPC32749
0.8408	Intermediate Similarity	NPC118427
0.8408	Intermediate Similarity	NPC70016
0.8408	Intermediate Similarity	NPC215921
0.8405	Intermediate Similarity	NPC327652
0.8405	Intermediate Similarity	NPC26386
0.8405	Intermediate Similarity	NPC471788
0.8397	Intermediate Similarity	NPC261322
0.8395	Intermediate Similarity	NPC215612
0.8387	Intermediate Similarity	NPC470757
0.8385	Intermediate Similarity	NPC141574
0.8385	Intermediate Similarity	NPC470358
0.8385	Intermediate Similarity	NPC155302
0.8385	Intermediate Similarity	NPC161947
0.8385	Intermediate Similarity	NPC21046
0.8385	Intermediate Similarity	NPC292415
0.8385	Intermediate Similarity	NPC36217
0.8377	Intermediate Similarity	NPC225351
0.8377	Intermediate Similarity	NPC75694
0.8375	Intermediate Similarity	NPC37543
0.8375	Intermediate Similarity	NPC179732
0.8375	Intermediate Similarity	NPC199463
0.8375	Intermediate Similarity	NPC178976
0.8373	Intermediate Similarity	NPC472620
0.8373	Intermediate Similarity	NPC158226
0.8366	Intermediate Similarity	NPC50954
0.8366	Intermediate Similarity	NPC469615
0.8365	Intermediate Similarity	NPC300757
0.8365	Intermediate Similarity	NPC180901
0.8365	Intermediate Similarity	NPC471456
0.8365	Intermediate Similarity	NPC38898
0.8364	Intermediate Similarity	NPC473095
0.8364	Intermediate Similarity	NPC473096
0.8364	Intermediate Similarity	NPC165979
0.8364	Intermediate Similarity	NPC163130
0.8354	Intermediate Similarity	NPC43319
0.8354	Intermediate Similarity	NPC207575
0.8354	Intermediate Similarity	NPC13481
0.8354	Intermediate Similarity	NPC470340
0.8354	Intermediate Similarity	NPC131121
0.8344	Intermediate Similarity	NPC306835
0.8344	Intermediate Similarity	NPC476477
0.8344	Intermediate Similarity	NPC476822
0.8344	Intermediate Similarity	NPC147596
0.8344	Intermediate Similarity	NPC216312
0.8344	Intermediate Similarity	NPC256463
0.8344	Intermediate Similarity	NPC29055
0.8344	Intermediate Similarity	NPC299405
0.8344	Intermediate Similarity	NPC111422
0.8344	Intermediate Similarity	NPC322021
0.8344	Intermediate Similarity	NPC471602
0.8344	Intermediate Similarity	NPC29771
0.8344	Intermediate Similarity	NPC96501
0.8344	Intermediate Similarity	NPC472279
0.8333	Intermediate Similarity	NPC470359
0.8333	Intermediate Similarity	NPC478222
0.8333	Intermediate Similarity	NPC349525
0.8333	Intermediate Similarity	NPC311740
0.8333	Intermediate Similarity	NPC87431
0.8333	Intermediate Similarity	NPC131905
0.8333	Intermediate Similarity	NPC470479
0.8323	Intermediate Similarity	NPC85121
0.8322	Intermediate Similarity	NPC470990
0.8313	Intermediate Similarity	NPC109827
0.8313	Intermediate Similarity	NPC77807
0.8313	Intermediate Similarity	NPC478027
0.8313	Intermediate Similarity	NPC474167
0.8313	Intermediate Similarity	NPC14561
0.8313	Intermediate Similarity	NPC470762
0.8313	Intermediate Similarity	NPC124470
0.8313	Intermediate Similarity	NPC5379
0.8313	Intermediate Similarity	NPC472803
0.8312	Intermediate Similarity	NPC309169
0.8312	Intermediate Similarity	NPC196941
0.8312	Intermediate Similarity	NPC113397
0.8303	Intermediate Similarity	NPC474024
0.8303	Intermediate Similarity	NPC218226
0.8303	Intermediate Similarity	NPC234331
0.8302	Intermediate Similarity	NPC475770
0.8302	Intermediate Similarity	NPC197188
0.8302	Intermediate Similarity	NPC43872
0.8302	Intermediate Similarity	NPC273248
0.8302	Intermediate Similarity	NPC144801
0.8302	Intermediate Similarity	NPC298802
0.8302	Intermediate Similarity	NPC238672
0.8302	Intermediate Similarity	NPC116850
0.8302	Intermediate Similarity	NPC25127
0.8302	Intermediate Similarity	NPC93552
0.8302	Intermediate Similarity	NPC291510
0.8293	Intermediate Similarity	NPC112981
0.8293	Intermediate Similarity	NPC178281
0.8293	Intermediate Similarity	NPC25361
0.8293	Intermediate Similarity	NPC146584
0.8293	Intermediate Similarity	NPC21016
0.8293	Intermediate Similarity	NPC303174
0.8291	Intermediate Similarity	NPC240768
0.8291	Intermediate Similarity	NPC200773
0.8282	Intermediate Similarity	NPC61594
0.8282	Intermediate Similarity	NPC201800
0.8282	Intermediate Similarity	NPC472964
0.8282	Intermediate Similarity	NPC56735
0.8274	Intermediate Similarity	NPC139350
0.8274	Intermediate Similarity	NPC294149
0.8272	Intermediate Similarity	NPC185617
0.8272	Intermediate Similarity	NPC84571
0.8272	Intermediate Similarity	NPC321399
0.8272	Intermediate Similarity	NPC472902
0.8272	Intermediate Similarity	NPC24627
0.8272	Intermediate Similarity	NPC130955
0.8269	Intermediate Similarity	NPC1580
0.8269	Intermediate Similarity	NPC127046
0.8269	Intermediate Similarity	NPC472969
0.8269	Intermediate Similarity	NPC52692
0.8267	Intermediate Similarity	NPC475111

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 NPC180388 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	936
0.2-0.3	1871
0.3-0.4	2507
0.4-0.5	1878
0.5-0.6	998
0.6-0.7	501
0.7-0.8	141
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8412	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD2532	Approved
0.8377	Intermediate Similarity	NPD2533	Approved
0.8377	Intermediate Similarity	NPD2534	Approved
0.8354	Intermediate Similarity	NPD7473	Discontinued
0.8282	Intermediate Similarity	NPD6232	Discontinued
0.8075	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD2346	Discontinued
0.8036	Intermediate Similarity	NPD5844	Phase 1
0.8012	Intermediate Similarity	NPD1934	Approved
0.7937	Intermediate Similarity	NPD3226	Approved
0.7907	Intermediate Similarity	NPD8313	Approved
0.7907	Intermediate Similarity	NPD8312	Approved
0.7885	Intermediate Similarity	NPD4628	Phase 3
0.787	Intermediate Similarity	NPD3818	Discontinued
0.7866	Intermediate Similarity	NPD3882	Suspended
0.7857	Intermediate Similarity	NPD2935	Discontinued
0.7853	Intermediate Similarity	NPD2801	Approved
0.7799	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD2799	Discontinued
0.7778	Intermediate Similarity	NPD4380	Phase 2
0.7771	Intermediate Similarity	NPD6234	Discontinued
0.7758	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD6166	Phase 2
0.7751	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7819	Suspended
0.7738	Intermediate Similarity	NPD5711	Approved
0.7738	Intermediate Similarity	NPD5710	Approved
0.7725	Intermediate Similarity	NPD5494	Approved
0.7712	Intermediate Similarity	NPD447	Suspended
0.7711	Intermediate Similarity	NPD7075	Discontinued
0.7697	Intermediate Similarity	NPD3817	Phase 2
0.7697	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6559	Discontinued
0.7683	Intermediate Similarity	NPD37	Approved
0.7674	Intermediate Similarity	NPD7074	Phase 3
0.767	Intermediate Similarity	NPD8150	Discontinued
0.7651	Intermediate Similarity	NPD4967	Phase 2
0.7651	Intermediate Similarity	NPD4966	Approved
0.7651	Intermediate Similarity	NPD4965	Approved
0.7644	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7054	Approved
0.7614	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6801	Discontinued
0.7572	Intermediate Similarity	NPD7472	Approved
0.7561	Intermediate Similarity	NPD6599	Discontinued
0.7558	Intermediate Similarity	NPD7228	Approved
0.7547	Intermediate Similarity	NPD8166	Discontinued
0.753	Intermediate Similarity	NPD1465	Phase 2
0.7516	Intermediate Similarity	NPD1511	Approved
0.7516	Intermediate Similarity	NPD2313	Discontinued
0.7516	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5402	Approved
0.7484	Intermediate Similarity	NPD230	Phase 1
0.7484	Intermediate Similarity	NPD2800	Approved
0.7484	Intermediate Similarity	NPD6674	Discontinued
0.7484	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6959	Discontinued
0.7471	Intermediate Similarity	NPD8127	Discontinued
0.7438	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3750	Approved
0.7438	Intermediate Similarity	NPD7003	Approved
0.7434	Intermediate Similarity	NPD9494	Approved
0.7429	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6797	Phase 2
0.7423	Intermediate Similarity	NPD1512	Approved
0.7419	Intermediate Similarity	NPD4060	Phase 1
0.7407	Intermediate Similarity	NPD6799	Approved
0.7405	Intermediate Similarity	NPD5408	Approved
0.7405	Intermediate Similarity	NPD5404	Approved
0.7405	Intermediate Similarity	NPD5405	Approved
0.7405	Intermediate Similarity	NPD5406	Approved
0.7396	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7458	Discontinued
0.7386	Intermediate Similarity	NPD7685	Pre-registration
0.7386	Intermediate Similarity	NPD7251	Discontinued
0.7374	Intermediate Similarity	NPD8434	Phase 2
0.7365	Intermediate Similarity	NPD4626	Approved
0.7362	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD919	Approved
0.7351	Intermediate Similarity	NPD1283	Approved
0.7345	Intermediate Similarity	NPD7808	Phase 3
0.7337	Intermediate Similarity	NPD7768	Phase 2
0.7329	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1607	Approved
0.7325	Intermediate Similarity	NPD6651	Approved
0.7317	Intermediate Similarity	NPD6273	Approved
0.7308	Intermediate Similarity	NPD2979	Phase 3
0.7305	Intermediate Similarity	NPD7411	Suspended
0.7301	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5691	Approved
0.7296	Intermediate Similarity	NPD2438	Suspended
0.7296	Intermediate Similarity	NPD1551	Phase 2
0.729	Intermediate Similarity	NPD7985	Registered
0.7287	Intermediate Similarity	NPD7435	Discontinued
0.7285	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6190	Approved
0.7278	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5403	Approved
0.725	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1510	Phase 2
0.7233	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3027	Phase 3
0.7222	Intermediate Similarity	NPD4110	Phase 3
0.7222	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6777	Approved
0.7219	Intermediate Similarity	NPD6780	Approved
0.7219	Intermediate Similarity	NPD6776	Approved
0.7219	Intermediate Similarity	NPD6779	Approved
0.7219	Intermediate Similarity	NPD6781	Approved
0.7219	Intermediate Similarity	NPD6778	Approved
0.7219	Intermediate Similarity	NPD6782	Approved
0.7216	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1549	Phase 2
0.7197	Intermediate Similarity	NPD1240	Approved
0.7197	Intermediate Similarity	NPD943	Approved
0.719	Intermediate Similarity	NPD1470	Approved
0.7188	Intermediate Similarity	NPD8151	Discontinued
0.7179	Intermediate Similarity	NPD3764	Approved
0.7168	Intermediate Similarity	NPD1247	Approved
0.7168	Intermediate Similarity	NPD7199	Phase 2
0.7152	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6355	Discontinued
0.7152	Intermediate Similarity	NPD1281	Approved
0.7152	Intermediate Similarity	NPD5401	Approved
0.7143	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6823	Phase 2
0.7143	Intermediate Similarity	NPD6005	Phase 3
0.7143	Intermediate Similarity	NPD5762	Approved
0.7143	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6004	Phase 3
0.7143	Intermediate Similarity	NPD2798	Approved
0.7143	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5763	Approved
0.7143	Intermediate Similarity	NPD6002	Phase 3
0.7143	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1653	Approved
0.7125	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3748	Approved
0.7101	Intermediate Similarity	NPD6386	Approved
0.7101	Intermediate Similarity	NPD6385	Approved
0.7095	Intermediate Similarity	NPD7240	Approved
0.7095	Intermediate Similarity	NPD7039	Approved
0.7095	Intermediate Similarity	NPD7038	Approved
0.7093	Intermediate Similarity	NPD3749	Approved
0.7089	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3620	Phase 2
0.7081	Intermediate Similarity	NPD2796	Approved
0.707	Intermediate Similarity	NPD411	Approved
0.7066	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD920	Approved
0.7062	Intermediate Similarity	NPD3751	Discontinued
0.7062	Intermediate Similarity	NPD7874	Approved
0.7062	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1933	Approved
0.7044	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD5124	Phase 1
0.7043	Intermediate Similarity	NPD6535	Approved
0.7043	Intermediate Similarity	NPD6534	Approved
0.7039	Intermediate Similarity	NPD1201	Approved
0.7037	Intermediate Similarity	NPD7266	Discontinued
0.7037	Intermediate Similarity	NPD2344	Approved
0.7032	Intermediate Similarity	NPD5647	Approved
0.7016	Intermediate Similarity	NPD7697	Approved
0.7016	Intermediate Similarity	NPD7696	Phase 3
0.7016	Intermediate Similarity	NPD7698	Approved
0.7	Intermediate Similarity	NPD9545	Approved
0.6993	Remote Similarity	NPD9717	Approved
0.6989	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD3926	Phase 2
0.6982	Remote Similarity	NPD3455	Phase 2
0.6981	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1613	Approved
0.698	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7871	Phase 2
0.6979	Remote Similarity	NPD8320	Phase 1
0.6979	Remote Similarity	NPD7870	Phase 2
0.6979	Remote Similarity	NPD8319	Approved
0.6977	Remote Similarity	NPD5353	Approved
0.6975	Remote Similarity	NPD2531	Phase 2
0.6968	Remote Similarity	NPD1203	Approved
0.6966	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7177	Discontinued
0.6962	Remote Similarity	NPD6798	Discontinued
0.6959	Remote Similarity	NPD7701	Phase 2
0.6954	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1651	Approved
0.6951	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5953	Discontinued
0.6943	Remote Similarity	NPD6832	Phase 2
0.6941	Remote Similarity	NPD7028	Phase 2
0.6939	Remote Similarity	NPD7782	Clinical (unspecified phase)

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