NPASS Compound

Structure

NPC473048 OpenBabel07101718192D 30 35 0 0 1 0 0 0 0 0999 V2000 -0.7661 2.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9825 4.4376 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 -5.9751 4.3299 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 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 3.5000 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 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 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 -1.7321 0.0000 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 -4.2007 1.7728 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 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8952 2.9757 0.0000 C 0 0 1 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 -4.3301 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8261 3.3410 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8376 2.2070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 28 1 0 0 0 0 5 6 2 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 18 2 0 0 0 0 9 19 2 0 0 0 0 10 14 1 0 0 0 0 10 21 1 0 0 0 0 11 15 1 0 0 0 0 11 20 1 0 0 0 0 12 25 1 0 0 0 0 14 24 1 0 0 0 0 15 26 1 0 0 0 0 16 18 1 0 0 0 0 16 22 1 0 0 0 0 17 27 1 0 0 0 0 17 29 1 0 0 0 0 18 19 1 0 0 0 0 19 30 1 0 0 0 0 20 24 1 6 0 0 0 20 27 1 0 0 0 0 21 25 1 6 0 0 0 21 27 1 0 0 0 0 22 24 1 6 0 0 0 22 26 1 0 0 0 0 23 25 1 6 0 0 0 23 28 1 0 0 0 0 23 29 1 0 0 0 0 24 1 1 6 0 0 0 25 2 1 1 0 0 0 26 3 1 6 0 0 0 26 30 1 0 0 0 0 27 13 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.28
Volume:	442.671
LogP:	6.192
LogD:	4.538
LogS:	-6.114
# Rotatable Bonds:	1
TPSA:	27.69
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.568
Synthetic Accessibility Score:	5.4
Fsp3:	0.778
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.9
MDCK Permeability:	2.0279328964534216e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.032
30% Bioavailability (F30%):	0.705

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.125
Plasma Protein Binding (PPB):	96.38141632080078%
Volume Distribution (VD):	1.44
Pgp-substrate:	2.2189645767211914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.061
CYP1A2-substrate:	0.69
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.927
CYP2C9-inhibitor:	0.221
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.323
CYP2D6-substrate:	0.641
CYP3A4-inhibitor:	0.885
CYP3A4-substrate:	0.649

ADMET: Excretion

Clearance (CL):	6.964
Half-life (T1/2):	0.127

ADMET: Toxicity

hERG Blockers:	0.653
Human Hepatotoxicity (H-HT):	0.593
Drug-inuced Liver Injury (DILI):	0.112
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.115
Maximum Recommended Daily Dose:	0.665
Skin Sensitization:	0.88
Carcinogencity:	0.2
Eye Corrosion:	0.012
Eye Irritation:	0.157
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC473048

Natural Product ID:	NPC473048
*Common Name:**	VYTRYBMUYJDNIN-RGCARSLISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VYTRYBMUYJDNIN-RGCARSLISA-N
Standard InCHI:	InChI=1S/C27H38O3/c1-24-14-10-21-25(2)12-7-13-27(21,17-29-23(25)28-4)20(24)11-15-26(3)22(24)16-18-8-5-6-9-19(18)30-26/h5-6,8-9,20-23H,7,10-17H2,1-4H3/t20-,21-,22-,23-,24+,25+,26-,27-/m0/s1
SMILES:	CC12CCC3C4(CCCC3(C1CCC5(C2CC6=CC=CC=C6O5)C)COC4OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3608572
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO33273	strongylophora strongilata	Species	n.a.	n.a.	n.a.	Iriomote Island	n.a.	PMID[26253631]

☑ 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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	8500.0	nM	PMID[466416]

☑ 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 NPC473048 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	559
0.1-0.2	1723
0.2-0.3	3929
0.3-0.4	8600
0.4-0.5	9366
0.5-0.6	11074
0.6-0.7	6851
0.7-0.8	576
0.8-0.85	13
0.85-0.9	1
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9248	High Similarity	NPC472792
0.9248	High Similarity	NPC472791
0.903	High Similarity	NPC473049
0.903	High Similarity	NPC472794
0.8661	High Similarity	NPC475839
0.8582	High Similarity	NPC211352
0.8571	High Similarity	NPC153019
0.8485	Intermediate Similarity	NPC223912
0.8485	Intermediate Similarity	NPC47288
0.8433	Intermediate Similarity	NPC473047
0.837	Intermediate Similarity	NPC27578
0.837	Intermediate Similarity	NPC289624
0.837	Intermediate Similarity	NPC321086
0.8333	Intermediate Similarity	NPC128321
0.8222	Intermediate Similarity	NPC472793
0.8214	Intermediate Similarity	NPC164743
0.8182	Intermediate Similarity	NPC248557
0.8143	Intermediate Similarity	NPC265335
0.8134	Intermediate Similarity	NPC186889
0.8134	Intermediate Similarity	NPC108164
0.8112	Intermediate Similarity	NPC474599
0.8085	Intermediate Similarity	NPC76312
0.806	Intermediate Similarity	NPC100414
0.806	Intermediate Similarity	NPC43000
0.8058	Intermediate Similarity	NPC137580
0.8041	Intermediate Similarity	NPC476452
0.8014	Intermediate Similarity	NPC95990
0.8	Intermediate Similarity	NPC474610
0.7987	Intermediate Similarity	NPC200645
0.7987	Intermediate Similarity	NPC106669
0.7987	Intermediate Similarity	NPC475227
0.7986	Intermediate Similarity	NPC96447
0.7972	Intermediate Similarity	NPC186033
0.7959	Intermediate Similarity	NPC470208
0.7959	Intermediate Similarity	NPC44452
0.7959	Intermediate Similarity	NPC295573
0.7958	Intermediate Similarity	NPC79372
0.7956	Intermediate Similarity	NPC196193
0.7956	Intermediate Similarity	NPC249425
0.7943	Intermediate Similarity	NPC306365
0.7926	Intermediate Similarity	NPC325294
0.7926	Intermediate Similarity	NPC321822
0.7907	Intermediate Similarity	NPC312105
0.7905	Intermediate Similarity	NPC183380
0.7899	Intermediate Similarity	NPC474200
0.7883	Intermediate Similarity	NPC96719
0.7883	Intermediate Similarity	NPC222108
0.7868	Intermediate Similarity	NPC473134
0.7862	Intermediate Similarity	NPC473575
0.7832	Intermediate Similarity	NPC221134
0.7823	Intermediate Similarity	NPC326801
0.781	Intermediate Similarity	NPC176590
0.78	Intermediate Similarity	NPC48671
0.7786	Intermediate Similarity	NPC24913
0.7786	Intermediate Similarity	NPC177712
0.7778	Intermediate Similarity	NPC108674
0.7778	Intermediate Similarity	NPC5155
0.7769	Intermediate Similarity	NPC33900
0.7762	Intermediate Similarity	NPC183781
0.7761	Intermediate Similarity	NPC473464
0.7761	Intermediate Similarity	NPC476332
0.7761	Intermediate Similarity	NPC152946
0.7755	Intermediate Similarity	NPC471608
0.7755	Intermediate Similarity	NPC475872
0.7746	Intermediate Similarity	NPC471522
0.7744	Intermediate Similarity	NPC212559
0.774	Intermediate Similarity	NPC133251
0.774	Intermediate Similarity	NPC471065
0.774	Intermediate Similarity	NPC471667
0.774	Intermediate Similarity	NPC217635
0.774	Intermediate Similarity	NPC79429
0.774	Intermediate Similarity	NPC253015
0.774	Intermediate Similarity	NPC164183
0.7733	Intermediate Similarity	NPC259707
0.773	Intermediate Similarity	NPC476615
0.773	Intermediate Similarity	NPC476616
0.773	Intermediate Similarity	NPC476617
0.773	Intermediate Similarity	NPC90083
0.773	Intermediate Similarity	NPC170779
0.773	Intermediate Similarity	NPC473107
0.7721	Intermediate Similarity	NPC17348
0.7714	Intermediate Similarity	NPC472798
0.771	Intermediate Similarity	NPC25648
0.7698	Intermediate Similarity	NPC325003
0.7692	Intermediate Similarity	NPC470308
0.7692	Intermediate Similarity	NPC196420
0.7692	Intermediate Similarity	NPC470307
0.7687	Intermediate Similarity	NPC476301
0.7687	Intermediate Similarity	NPC43508
0.7687	Intermediate Similarity	NPC90645
0.7687	Intermediate Similarity	NPC286245
0.7687	Intermediate Similarity	NPC272619
0.7682	Intermediate Similarity	NPC233467
0.7682	Intermediate Similarity	NPC59692
0.7682	Intermediate Similarity	NPC325860
0.7676	Intermediate Similarity	NPC79957
0.7671	Intermediate Similarity	NPC116922
0.766	Intermediate Similarity	NPC138940
0.766	Intermediate Similarity	NPC77196
0.766	Intermediate Similarity	NPC469610
0.7655	Intermediate Similarity	NPC138149
0.7651	Intermediate Similarity	NPC179809
0.7647	Intermediate Similarity	NPC256015
0.7647	Intermediate Similarity	NPC294156
0.7643	Intermediate Similarity	NPC244888
0.7643	Intermediate Similarity	NPC68205
0.7643	Intermediate Similarity	NPC284232
0.7643	Intermediate Similarity	NPC472590
0.7643	Intermediate Similarity	NPC118683
0.7643	Intermediate Similarity	NPC164804
0.7643	Intermediate Similarity	NPC293203
0.7643	Intermediate Similarity	NPC211413
0.7635	Intermediate Similarity	NPC102280
0.7635	Intermediate Similarity	NPC155564
0.7635	Intermediate Similarity	NPC248053
0.763	Intermediate Similarity	NPC188997
0.763	Intermediate Similarity	NPC150026
0.7626	Intermediate Similarity	NPC472797
0.7626	Intermediate Similarity	NPC93962
0.7622	Intermediate Similarity	NPC469383
0.7622	Intermediate Similarity	NPC475628
0.7622	Intermediate Similarity	NPC472800
0.7619	Intermediate Similarity	NPC225445
0.7619	Intermediate Similarity	NPC177597
0.7619	Intermediate Similarity	NPC472155
0.7619	Intermediate Similarity	NPC471063
0.7609	Intermediate Similarity	NPC177167
0.7603	Intermediate Similarity	NPC93640
0.7603	Intermediate Similarity	NPC323126
0.7603	Intermediate Similarity	NPC472353
0.7603	Intermediate Similarity	NPC20631
0.7594	Intermediate Similarity	NPC51341
0.7594	Intermediate Similarity	NPC59561
0.7594	Intermediate Similarity	NPC172253
0.7591	Intermediate Similarity	NPC124030
0.7591	Intermediate Similarity	NPC4286
0.7591	Intermediate Similarity	NPC76119
0.7589	Intermediate Similarity	NPC85595
0.7589	Intermediate Similarity	NPC469611
0.7586	Intermediate Similarity	NPC193920
0.7584	Intermediate Similarity	NPC224674
0.7584	Intermediate Similarity	NPC275284
0.7584	Intermediate Similarity	NPC31325
0.7584	Intermediate Similarity	NPC114505
0.7584	Intermediate Similarity	NPC15956
0.7584	Intermediate Similarity	NPC193473
0.7584	Intermediate Similarity	NPC213074
0.7574	Intermediate Similarity	NPC261992
0.7569	Intermediate Similarity	NPC87777
0.7569	Intermediate Similarity	NPC262328
0.7569	Intermediate Similarity	NPC134260
0.7568	Intermediate Similarity	NPC472457
0.7568	Intermediate Similarity	NPC173630
0.7568	Intermediate Similarity	NPC23807
0.7566	Intermediate Similarity	NPC21902
0.7566	Intermediate Similarity	NPC474442
0.7556	Intermediate Similarity	NPC48623
0.7556	Intermediate Similarity	NPC168707
0.7554	Intermediate Similarity	NPC53986
0.7554	Intermediate Similarity	NPC38664
0.755	Intermediate Similarity	NPC182368
0.755	Intermediate Similarity	NPC469706
0.755	Intermediate Similarity	NPC9933
0.755	Intermediate Similarity	NPC214326
0.755	Intermediate Similarity	NPC185955
0.755	Intermediate Similarity	NPC260781
0.755	Intermediate Similarity	NPC469707
0.755	Intermediate Similarity	NPC145979
0.755	Intermediate Similarity	NPC158784
0.755	Intermediate Similarity	NPC225815
0.755	Intermediate Similarity	NPC218041
0.755	Intermediate Similarity	NPC98624
0.7537	Intermediate Similarity	NPC474131
0.7537	Intermediate Similarity	NPC260832
0.7537	Intermediate Similarity	NPC135467
0.7536	Intermediate Similarity	NPC283049
0.7536	Intermediate Similarity	NPC50315
0.7536	Intermediate Similarity	NPC230479
0.7536	Intermediate Similarity	NPC26879
0.7534	Intermediate Similarity	NPC210192
0.7533	Intermediate Similarity	NPC290902
0.7533	Intermediate Similarity	NPC474795
0.7533	Intermediate Similarity	NPC130959
0.7533	Intermediate Similarity	NPC117788
0.7533	Intermediate Similarity	NPC291326
0.7533	Intermediate Similarity	NPC270751
0.7533	Intermediate Similarity	NPC474856
0.7533	Intermediate Similarity	NPC220282
0.7533	Intermediate Similarity	NPC474834
0.7533	Intermediate Similarity	NPC474940
0.7533	Intermediate Similarity	NPC303013
0.7533	Intermediate Similarity	NPC212142
0.7533	Intermediate Similarity	NPC159697
0.7532	Intermediate Similarity	NPC25889
0.7519	Intermediate Similarity	NPC470723
0.7518	Intermediate Similarity	NPC75432
0.7518	Intermediate Similarity	NPC265413
0.7518	Intermediate Similarity	NPC10154
0.7518	Intermediate Similarity	NPC8899
0.7518	Intermediate Similarity	NPC61685

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 NPC473048 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	459
0.1-0.2	901
0.2-0.3	1665
0.3-0.4	2860
0.4-0.5	1864
0.5-0.6	1020
0.6-0.7	359
0.7-0.8	22
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
0.8106	Intermediate Similarity	NPD5327	Phase 3
0.7902	Intermediate Similarity	NPD6674	Discontinued
0.7826	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD4908	Phase 1
0.7676	Intermediate Similarity	NPD7097	Phase 1
0.7676	Intermediate Similarity	NPD7119	Phase 2
0.766	Intermediate Similarity	NPD5735	Approved
0.7606	Intermediate Similarity	NPD6353	Approved
0.7589	Intermediate Similarity	NPD4140	Approved
0.7518	Intermediate Similarity	NPD8651	Approved
0.7518	Intermediate Similarity	NPD8032	Phase 2
0.75	Intermediate Similarity	NPD4625	Phase 3
0.7482	Intermediate Similarity	NPD2861	Phase 2
0.7468	Intermediate Similarity	NPD8455	Phase 2
0.7463	Intermediate Similarity	NPD5691	Approved
0.7447	Intermediate Similarity	NPD7294	Phase 1
0.7447	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD4749	Approved
0.7426	Intermediate Similarity	NPD1610	Phase 2
0.7424	Intermediate Similarity	NPD6671	Approved
0.7424	Intermediate Similarity	NPD7157	Approved
0.741	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4624	Approved
0.7391	Intermediate Similarity	NPD6696	Suspended
0.7379	Intermediate Similarity	NPD4108	Discontinued
0.7333	Intermediate Similarity	NPD5585	Approved
0.7329	Intermediate Similarity	NPD6099	Approved
0.7329	Intermediate Similarity	NPD6100	Approved
0.7328	Intermediate Similarity	NPD5535	Approved
0.732	Intermediate Similarity	NPD7458	Discontinued
0.7299	Intermediate Similarity	NPD1091	Approved
0.7299	Intermediate Similarity	NPD3705	Approved
0.7293	Intermediate Similarity	NPD6387	Discontinued
0.7279	Intermediate Similarity	NPD1778	Approved
0.7254	Intermediate Similarity	NPD7095	Approved
0.7252	Intermediate Similarity	NPD1139	Approved
0.7252	Intermediate Similarity	NPD1137	Approved
0.7248	Intermediate Similarity	NPD7466	Approved
0.7222	Intermediate Similarity	NPD4060	Phase 1
0.7206	Intermediate Similarity	NPD3445	Approved
0.7206	Intermediate Similarity	NPD3443	Approved
0.7206	Intermediate Similarity	NPD3444	Approved
0.7197	Intermediate Similarity	NPD1138	Approved
0.719	Intermediate Similarity	NPD4727	Phase 1
0.7185	Intermediate Similarity	NPD7644	Approved
0.7181	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD1611	Approved
0.7171	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5763	Approved
0.7162	Intermediate Similarity	NPD5762	Approved
0.7154	Intermediate Similarity	NPD2684	Approved
0.7153	Intermediate Similarity	NPD4626	Approved
0.7143	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5283	Phase 1
0.7133	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD7003	Approved
0.7124	Intermediate Similarity	NPD6273	Approved
0.7123	Intermediate Similarity	NPD4097	Suspended
0.7111	Intermediate Similarity	NPD7340	Approved
0.7103	Intermediate Similarity	NPD3109	Approved
0.7103	Intermediate Similarity	NPD3110	Approved
0.7099	Intermediate Similarity	NPD5451	Approved
0.708	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4359	Approved
0.7071	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7843	Approved
0.7037	Intermediate Similarity	NPD709	Approved
0.7037	Intermediate Similarity	NPD2557	Approved
0.7029	Intermediate Similarity	NPD17	Approved
0.7024	Intermediate Similarity	NPD8313	Approved
0.7024	Intermediate Similarity	NPD8312	Approved
0.7021	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6580	Approved
0.7007	Intermediate Similarity	NPD6581	Approved
0.7007	Intermediate Similarity	NPD1548	Phase 1
0.7	Intermediate Similarity	NPD7037	Approved
0.6986	Remote Similarity	NPD3620	Phase 2
0.6986	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3496	Discontinued
0.697	Remote Similarity	NPD7228	Approved
0.6957	Remote Similarity	NPD1651	Approved
0.6939	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD3657	Discovery
0.6939	Remote Similarity	NPD5124	Phase 1
0.6939	Remote Similarity	NPD6355	Discontinued
0.6929	Remote Similarity	NPD1281	Approved
0.6928	Remote Similarity	NPD5058	Phase 3
0.6923	Remote Similarity	NPD6584	Phase 3
0.6918	Remote Similarity	NPD7265	Discontinued
0.6906	Remote Similarity	NPD6516	Phase 2
0.6906	Remote Similarity	NPD5846	Approved
0.6889	Remote Similarity	NPD1398	Phase 1
0.6884	Remote Similarity	NPD3091	Approved
0.6879	Remote Similarity	NPD2233	Approved
0.6879	Remote Similarity	NPD1608	Approved
0.6879	Remote Similarity	NPD2232	Approved
0.6879	Remote Similarity	NPD2230	Approved
0.6875	Remote Similarity	NPD5736	Approved
0.6875	Remote Similarity	NPD2237	Approved
0.6871	Remote Similarity	NPD8127	Discontinued
0.6871	Remote Similarity	NPD2979	Phase 3
0.687	Remote Similarity	NPD3134	Approved
0.6863	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD3596	Phase 2
0.6855	Remote Similarity	NPD5722	Discontinued
0.6853	Remote Similarity	NPD4098	Discontinued
0.6853	Remote Similarity	NPD2797	Approved
0.6849	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD6798	Discontinued
0.6846	Remote Similarity	NPD2200	Suspended
0.6839	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7447	Phase 1
0.6835	Remote Similarity	NPD1357	Approved
0.6835	Remote Similarity	NPD3049	Approved
0.6835	Remote Similarity	NPD7028	Phase 2
0.6831	Remote Similarity	NPD6582	Phase 2
0.6831	Remote Similarity	NPD6583	Phase 3
0.6831	Remote Similarity	NPD3685	Discontinued
0.6829	Remote Similarity	NPD3787	Discontinued
0.6829	Remote Similarity	NPD3051	Approved
0.6824	Remote Similarity	NPD4622	Approved
0.6824	Remote Similarity	NPD4618	Approved
0.6821	Remote Similarity	NPD7030	Discontinued
0.6818	Remote Similarity	NPD290	Approved
0.6818	Remote Similarity	NPD6666	Approved
0.6818	Remote Similarity	NPD6667	Approved
0.6809	Remote Similarity	NPD3092	Approved
0.6806	Remote Similarity	NPD2798	Approved
0.6805	Remote Similarity	NPD7240	Approved
0.6803	Remote Similarity	NPD4474	Approved
0.6803	Remote Similarity	NPD4475	Approved
0.6803	Remote Similarity	NPD4870	Approved
0.6797	Remote Similarity	NPD8166	Discontinued
0.6795	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2667	Approved
0.6786	Remote Similarity	NPD3095	Discontinued
0.6786	Remote Similarity	NPD2668	Approved
0.6783	Remote Similarity	NPD1283	Approved
0.6779	Remote Similarity	NPD2157	Approved
0.6779	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7041	Phase 2
0.6774	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7199	Phase 2
0.6763	Remote Similarity	NPD7741	Discontinued
0.6759	Remote Similarity	NPD1712	Approved
0.6757	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2238	Phase 2
0.6757	Remote Similarity	NPD1613	Approved
0.6755	Remote Similarity	NPD4476	Approved
0.6755	Remote Similarity	NPD4477	Approved
0.6752	Remote Similarity	NPD7427	Discontinued
0.675	Remote Similarity	NPD37	Approved
0.6747	Remote Similarity	NPD4481	Phase 3
0.6742	Remote Similarity	NPD968	Approved
0.6736	Remote Similarity	NPD3267	Approved
0.6736	Remote Similarity	NPD3266	Approved
0.6735	Remote Similarity	NPD7985	Registered
0.6733	Remote Similarity	NPD5689	Approved
0.6733	Remote Similarity	NPD5688	Approved
0.6732	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD4965	Approved
0.6728	Remote Similarity	NPD4966	Approved
0.6728	Remote Similarity	NPD4967	Phase 2
0.6726	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD6382	Discontinued
0.6713	Remote Similarity	NPD6543	Approved
0.6713	Remote Similarity	NPD6542	Approved
0.6713	Remote Similarity	NPD6540	Phase 3
0.6713	Remote Similarity	NPD6539	Approved
0.6712	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7266	Discontinued
0.671	Remote Similarity	NPD6815	Approved
0.6708	Remote Similarity	NPD7819	Suspended
0.6691	Remote Similarity	NPD821	Approved
0.669	Remote Similarity	NPD3690	Phase 2
0.669	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.669	Remote Similarity	NPD3691	Phase 2
0.6689	Remote Similarity	NPD6663	Approved
0.6689	Remote Similarity	NPD7033	Discontinued
0.6689	Remote Similarity	NPD7477	Discontinued
0.6689	Remote Similarity	NPD3748	Approved
0.6688	Remote Similarity	NPD4110	Phase 3
0.6688	Remote Similarity	NPD4628	Phase 3
0.6688	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2969	Approved
0.6687	Remote Similarity	NPD7833	Phase 2
0.6687	Remote Similarity	NPD2970	Approved
0.6687	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7831	Phase 2
0.6687	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7074	Phase 3
0.6667	Remote Similarity	NPD6538	Approved
0.6667	Remote Similarity	NPD7212	Phase 2
0.6667	Remote Similarity	NPD2556	Approved
0.6667	Remote Similarity	NPD6541	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