NPASS Compound

Structure

NPC57272 OpenBabel07101718222D 25 29 0 0 1 0 0 0 0 0999 V2000 1.0895 4.1676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1695 1.1182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2889 1.5920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9909 0.1342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0567 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0567 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0790 1.7594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4339 -0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4615 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1906 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1906 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4088 -1.1235 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9227 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9227 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5789 2.5125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4088 1.1235 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4985 2.1195 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4339 0.9010 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6313 -2.0984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3569 2.6324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6761 -0.7368 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3564 3.4874 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8738 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8738 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 4 19 1 0 0 0 0 5 10 2 0 0 0 0 5 13 1 0 0 0 0 6 11 2 0 0 0 0 6 14 1 0 0 0 0 7 15 2 0 0 0 0 7 18 1 0 0 0 0 8 12 1 0 0 0 0 8 19 1 0 0 0 0 9 24 1 0 0 0 0 9 25 1 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 11 16 1 0 0 0 0 12 20 1 1 0 0 0 13 14 2 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 18 1 1 0 0 0 17 21 1 1 0 0 0 18 3 1 6 0 0 0 18 19 1 0 0 0 0 19 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	347.14
Volume:	330.294
LogP:	-0.191
LogD:	-0.099
LogS:	-2.042
# Rotatable Bonds:	1
TPSA:	91.21
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.588
Synthetic Accessibility Score:	5.373
Fsp3:	0.556
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:	-5.647
MDCK Permeability:	5.285027509671636e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.347
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.288
Plasma Protein Binding (PPB):	17.658246994018555%
Volume Distribution (VD):	2.341
Pgp-substrate:	73.779541015625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.495
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.863
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.328
CYP2D6-inhibitor:	0.053
CYP2D6-substrate:	0.168
CYP3A4-inhibitor:	0.339
CYP3A4-substrate:	0.893

ADMET: Excretion

Clearance (CL):	5.348
Half-life (T1/2):	0.935

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.636
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.08
Rat Oral Acute Toxicity:	0.91
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.14
Carcinogencity:	0.877
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.894

Download Data

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

Natural Product: NPC57272

Natural Product ID:	NPC57272
*Common Name:**	INVLOFKFVTTYSR-DQDQBAQVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	INVLOFKFVTTYSR-DQDQBAQVSA-N
Standard InCHI:	InChI=1S/C18H21NO6/c1-23-15-7-18-3-2-4-19(18,22)8-12(20)10-5-13-14(25-9-24-13)6-11(10)16(18)17(15)21/h5-7,12,16-17,20-21H,2-4,8-9H2,1H3/t12-,16+,17+,18-,19+/m0/s1
SMILES:	COC1=C[C@@]23CCC[N@@]3(=O)C[C@@H](c3cc4c(cc3[C@@H]2[C@@H]1O)OCO4)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464201
PubChem CID:	10958964
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003778] Cephalotaxus alkaloids

*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
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542368]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28139925]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31184894]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	31.0	ug.mL-1	PMID[527337]

☑ 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 NPC57272 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	264
0.1-0.2	1313
0.2-0.3	4930
0.3-0.4	12637
0.4-0.5	8342
0.5-0.6	11349
0.6-0.7	3179
0.7-0.8	591
0.8-0.85	59
0.85-0.9	28
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9809	High Similarity	NPC298186
0.9809	High Similarity	NPC301189
0.8889	High Similarity	NPC165797
0.8788	High Similarity	NPC476002
0.8402	Intermediate Similarity	NPC100566
0.8363	Intermediate Similarity	NPC225597
0.8363	Intermediate Similarity	NPC470739
0.8363	Intermediate Similarity	NPC477640
0.8323	Intermediate Similarity	NPC4304
0.8304	Intermediate Similarity	NPC474475
0.8294	Intermediate Similarity	NPC252960
0.8294	Intermediate Similarity	NPC190332
0.8294	Intermediate Similarity	NPC181653
0.8246	Intermediate Similarity	NPC158148
0.8246	Intermediate Similarity	NPC82533
0.8246	Intermediate Similarity	NPC290759
0.8246	Intermediate Similarity	NPC475686
0.8246	Intermediate Similarity	NPC58766
0.8246	Intermediate Similarity	NPC266176
0.8225	Intermediate Similarity	NPC218614
0.8167	Intermediate Similarity	NPC319549
0.8155	Intermediate Similarity	NPC92191
0.8155	Intermediate Similarity	NPC59028
0.8118	Intermediate Similarity	NPC320104
0.8114	Intermediate Similarity	NPC237044
0.8068	Intermediate Similarity	NPC474325
0.8057	Intermediate Similarity	NPC187678
0.8057	Intermediate Similarity	NPC304675
0.8034	Intermediate Similarity	NPC233718
0.8023	Intermediate Similarity	NPC474745
0.8011	Intermediate Similarity	NPC474470
0.8	Intermediate Similarity	NPC2314
0.7988	Intermediate Similarity	NPC475326
0.7955	Intermediate Similarity	NPC49353
0.7931	Intermediate Similarity	NPC160570
0.7921	Intermediate Similarity	NPC99179
0.7921	Intermediate Similarity	NPC244554
0.7895	Intermediate Similarity	NPC97072
0.7895	Intermediate Similarity	NPC249274
0.7895	Intermediate Similarity	NPC205167
0.7895	Intermediate Similarity	NPC215829
0.7889	Intermediate Similarity	NPC475981
0.7889	Intermediate Similarity	NPC474746
0.7886	Intermediate Similarity	NPC311991
0.7857	Intermediate Similarity	NPC148898
0.7802	Intermediate Similarity	NPC230098
0.7784	Intermediate Similarity	NPC329911
0.7771	Intermediate Similarity	NPC474324
0.7771	Intermediate Similarity	NPC57812
0.7759	Intermediate Similarity	NPC180306
0.7759	Intermediate Similarity	NPC76116
0.7738	Intermediate Similarity	NPC274026
0.7733	Intermediate Similarity	NPC69360
0.7727	Intermediate Similarity	NPC475845
0.7727	Intermediate Similarity	NPC164429
0.7684	Intermediate Similarity	NPC474708
0.7674	Intermediate Similarity	NPC148014
0.7674	Intermediate Similarity	NPC40389
0.7674	Intermediate Similarity	NPC78359
0.7674	Intermediate Similarity	NPC65490
0.7674	Intermediate Similarity	NPC315707
0.7667	Intermediate Similarity	NPC15919
0.7667	Intermediate Similarity	NPC118633
0.7667	Intermediate Similarity	NPC148693
0.7667	Intermediate Similarity	NPC294790
0.7661	Intermediate Similarity	NPC78733
0.7657	Intermediate Similarity	NPC247972
0.7647	Intermediate Similarity	NPC133011
0.7647	Intermediate Similarity	NPC33256
0.7647	Intermediate Similarity	NPC82285
0.7637	Intermediate Similarity	NPC248642
0.7616	Intermediate Similarity	NPC160931
0.7616	Intermediate Similarity	NPC37205
0.7616	Intermediate Similarity	NPC147091
0.7596	Intermediate Similarity	NPC156576
0.7586	Intermediate Similarity	NPC18402
0.7584	Intermediate Similarity	NPC75958
0.7557	Intermediate Similarity	NPC231198
0.7554	Intermediate Similarity	NPC9867
0.7544	Intermediate Similarity	NPC37272
0.7529	Intermediate Similarity	NPC111485
0.7527	Intermediate Similarity	NPC126284
0.7486	Intermediate Similarity	NPC474953
0.7472	Intermediate Similarity	NPC150879
0.7471	Intermediate Similarity	NPC129603
0.7458	Intermediate Similarity	NPC238530
0.7458	Intermediate Similarity	NPC232514
0.7458	Intermediate Similarity	NPC89199
0.7458	Intermediate Similarity	NPC54125
0.7458	Intermediate Similarity	NPC276944
0.7447	Intermediate Similarity	NPC94499
0.7444	Intermediate Similarity	NPC65403
0.7442	Intermediate Similarity	NPC270811
0.7442	Intermediate Similarity	NPC223124
0.7442	Intermediate Similarity	NPC471073
0.744	Intermediate Similarity	NPC130926
0.743	Intermediate Similarity	NPC182257
0.7412	Intermediate Similarity	NPC475959
0.7401	Intermediate Similarity	NPC124433
0.7401	Intermediate Similarity	NPC293871
0.7377	Intermediate Similarity	NPC114364
0.7377	Intermediate Similarity	NPC320223
0.7374	Intermediate Similarity	NPC304846
0.7363	Intermediate Similarity	NPC128560
0.7363	Intermediate Similarity	NPC229166
0.7363	Intermediate Similarity	NPC199465
0.7351	Intermediate Similarity	NPC275132
0.7341	Intermediate Similarity	NPC233029
0.7341	Intermediate Similarity	NPC210148
0.7326	Intermediate Similarity	NPC214116
0.7326	Intermediate Similarity	NPC223125
0.7318	Intermediate Similarity	NPC124657
0.7317	Intermediate Similarity	NPC475828
0.7314	Intermediate Similarity	NPC146288
0.7308	Intermediate Similarity	NPC228040
0.7303	Intermediate Similarity	NPC233650
0.7297	Intermediate Similarity	NPC474607
0.7296	Intermediate Similarity	NPC80472
0.7278	Intermediate Similarity	NPC210140
0.7273	Intermediate Similarity	NPC7018
0.7263	Intermediate Similarity	NPC134858
0.7258	Intermediate Similarity	NPC474650
0.7257	Intermediate Similarity	NPC41178
0.7257	Intermediate Similarity	NPC216459
0.7257	Intermediate Similarity	NPC138487
0.7234	Intermediate Similarity	NPC162694
0.7228	Intermediate Similarity	NPC283999
0.7216	Intermediate Similarity	NPC234392
0.7216	Intermediate Similarity	NPC477133
0.7216	Intermediate Similarity	NPC477132
0.7216	Intermediate Similarity	NPC31311
0.7213	Intermediate Similarity	NPC110374
0.7213	Intermediate Similarity	NPC289743
0.7209	Intermediate Similarity	NPC24233
0.7209	Intermediate Similarity	NPC246587
0.7209	Intermediate Similarity	NPC59907
0.7209	Intermediate Similarity	NPC37144
0.7209	Intermediate Similarity	NPC135538
0.7209	Intermediate Similarity	NPC428
0.7209	Intermediate Similarity	NPC147390
0.7209	Intermediate Similarity	NPC476571
0.7207	Intermediate Similarity	NPC59567
0.7196	Intermediate Similarity	NPC141440
0.7195	Intermediate Similarity	NPC219671
0.7195	Intermediate Similarity	NPC104077
0.7195	Intermediate Similarity	NPC259742
0.7195	Intermediate Similarity	NPC147616
0.7189	Intermediate Similarity	NPC477560
0.7182	Intermediate Similarity	NPC210918
0.7182	Intermediate Similarity	NPC247389
0.7169	Intermediate Similarity	NPC174191
0.7168	Intermediate Similarity	NPC211296
0.7167	Intermediate Similarity	NPC302527
0.7167	Intermediate Similarity	NPC167546
0.7167	Intermediate Similarity	NPC16805
0.7166	Intermediate Similarity	NPC476575
0.7166	Intermediate Similarity	NPC116284
0.7151	Intermediate Similarity	NPC179825
0.7151	Intermediate Similarity	NPC321505
0.7151	Intermediate Similarity	NPC475794
0.7151	Intermediate Similarity	NPC191376
0.7143	Intermediate Similarity	NPC286135
0.7143	Intermediate Similarity	NPC204908
0.7143	Intermediate Similarity	NPC83198
0.7143	Intermediate Similarity	NPC77572
0.7136	Intermediate Similarity	NPC329329
0.7136	Intermediate Similarity	NPC317709
0.7135	Intermediate Similarity	NPC477080
0.7135	Intermediate Similarity	NPC1291
0.7135	Intermediate Similarity	NPC115343
0.7135	Intermediate Similarity	NPC185838
0.7128	Intermediate Similarity	NPC135772
0.7127	Intermediate Similarity	NPC219341
0.7127	Intermediate Similarity	NPC24264
0.7127	Intermediate Similarity	NPC476432
0.7126	Intermediate Similarity	NPC88249
0.7126	Intermediate Similarity	NPC192768
0.7126	Intermediate Similarity	NPC97221
0.7126	Intermediate Similarity	NPC220858
0.7126	Intermediate Similarity	NPC151895
0.712	Intermediate Similarity	NPC152680
0.712	Intermediate Similarity	NPC190783
0.712	Intermediate Similarity	NPC232386
0.7119	Intermediate Similarity	NPC323443
0.7119	Intermediate Similarity	NPC180756
0.7112	Intermediate Similarity	NPC155442
0.7112	Intermediate Similarity	NPC476574
0.7112	Intermediate Similarity	NPC477561
0.7112	Intermediate Similarity	NPC305847
0.7112	Intermediate Similarity	NPC312918
0.7091	Intermediate Similarity	NPC471505
0.7091	Intermediate Similarity	NPC106739
0.7091	Intermediate Similarity	NPC97316
0.7088	Intermediate Similarity	NPC298979
0.7083	Intermediate Similarity	NPC117717
0.7076	Intermediate Similarity	NPC265154
0.7074	Intermediate Similarity	NPC302449
0.7072	Intermediate Similarity	NPC169743
0.7072	Intermediate Similarity	NPC225774
0.7072	Intermediate Similarity	NPC24465

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 NPC57272 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	624
0.2-0.3	1314
0.3-0.4	2620
0.4-0.5	2456
0.5-0.6	1423
0.6-0.7	473
0.7-0.8	68
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
0.8167	Intermediate Similarity	NPD7296	Approved
0.7719	Intermediate Similarity	NPD2978	Approved
0.7719	Intermediate Similarity	NPD2977	Approved
0.7674	Intermediate Similarity	NPD2563	Approved
0.7674	Intermediate Similarity	NPD2560	Approved
0.747	Intermediate Similarity	NPD4236	Phase 3
0.747	Intermediate Similarity	NPD4237	Approved
0.7427	Intermediate Similarity	NPD4210	Discontinued
0.7416	Intermediate Similarity	NPD6071	Discontinued
0.7381	Intermediate Similarity	NPD5241	Discontinued
0.7374	Intermediate Similarity	NPD2970	Approved
0.7374	Intermediate Similarity	NPD2969	Approved
0.7314	Intermediate Similarity	NPD5773	Approved
0.7314	Intermediate Similarity	NPD5772	Approved
0.7278	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD2489	Approved
0.7238	Intermediate Similarity	NPD27	Approved
0.7222	Intermediate Similarity	NPD3051	Approved
0.72	Intermediate Similarity	NPD4772	Phase 2
0.72	Intermediate Similarity	NPD4773	Phase 2
0.716	Intermediate Similarity	NPD3060	Approved
0.7143	Intermediate Similarity	NPD1375	Discontinued
0.7135	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD7311	Approved
0.7112	Intermediate Similarity	NPD7313	Approved
0.7112	Intermediate Similarity	NPD7312	Approved
0.7112	Intermediate Similarity	NPD7310	Approved
0.709	Intermediate Similarity	NPD4663	Approved
0.7074	Intermediate Similarity	NPD7309	Approved
0.7053	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7906	Approved
0.7029	Intermediate Similarity	NPD3687	Approved
0.7029	Intermediate Similarity	NPD3686	Approved
0.7021	Intermediate Similarity	NPD4577	Approved
0.7021	Intermediate Similarity	NPD4578	Approved
0.701	Intermediate Similarity	NPD5582	Discontinued
0.7	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD2238	Phase 2
0.6984	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2677	Approved
0.6959	Remote Similarity	NPD4162	Approved
0.6957	Remote Similarity	NPD4481	Phase 3
0.6954	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3705	Approved
0.6931	Remote Similarity	NPD7280	Phase 3
0.6931	Remote Similarity	NPD7281	Phase 3
0.6928	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD2161	Phase 2
0.6879	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4584	Approved
0.6853	Remote Similarity	NPD4420	Approved
0.6813	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5006	Approved
0.68	Remote Similarity	NPD5005	Approved
0.6798	Remote Similarity	NPD4005	Discontinued
0.6793	Remote Similarity	NPD6107	Approved
0.6763	Remote Similarity	NPD5177	Phase 3
0.6761	Remote Similarity	NPD3158	Phase 1
0.6761	Remote Similarity	NPD3157	Approved
0.6761	Remote Similarity	NPD4123	Phase 3
0.6734	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD1132	Approved
0.6726	Remote Similarity	NPD1130	Approved
0.6726	Remote Similarity	NPD1136	Approved
0.6723	Remote Similarity	NPD7526	Approved
0.6723	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD52	Approved
0.6721	Remote Similarity	NPD7833	Phase 2
0.6721	Remote Similarity	NPD7831	Phase 2
0.6721	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5604	Discontinued
0.6705	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD1774	Approved
0.6685	Remote Similarity	NPD3639	Approved
0.6685	Remote Similarity	NPD3640	Phase 3
0.6685	Remote Similarity	NPD3641	Approved
0.6684	Remote Similarity	NPD2898	Approved
0.6667	Remote Similarity	NPD597	Approved
0.6667	Remote Similarity	NPD4010	Discontinued
0.6667	Remote Similarity	NPD601	Approved
0.6667	Remote Similarity	NPD6896	Approved
0.6667	Remote Similarity	NPD598	Approved
0.6667	Remote Similarity	NPD6895	Approved
0.6667	Remote Similarity	NPD7827	Phase 1
0.6649	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7124	Phase 2
0.6647	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD8054	Approved
0.6632	Remote Similarity	NPD8053	Approved
0.6627	Remote Similarity	NPD2674	Phase 3
0.6615	Remote Similarity	NPD6842	Approved
0.6615	Remote Similarity	NPD6843	Phase 3
0.6615	Remote Similarity	NPD6841	Approved
0.6608	Remote Similarity	NPD817	Approved
0.6608	Remote Similarity	NPD823	Approved
0.6597	Remote Similarity	NPD7007	Discovery
0.6593	Remote Similarity	NPD7298	Approved
0.6591	Remote Similarity	NPD3692	Discontinued
0.6588	Remote Similarity	NPD3061	Approved
0.6588	Remote Similarity	NPD3062	Approved
0.6588	Remote Similarity	NPD3059	Approved
0.6585	Remote Similarity	NPD2230	Approved
0.6585	Remote Similarity	NPD2232	Approved
0.6585	Remote Similarity	NPD2233	Approved
0.6584	Remote Similarity	NPD3452	Approved
0.6584	Remote Similarity	NPD2493	Approved
0.6584	Remote Similarity	NPD3450	Approved
0.6584	Remote Similarity	NPD2494	Approved
0.6575	Remote Similarity	NPD4675	Approved
0.6575	Remote Similarity	NPD6876	Approved
0.6575	Remote Similarity	NPD6875	Approved
0.6575	Remote Similarity	NPD4678	Approved
0.657	Remote Similarity	NPD6111	Discontinued
0.6569	Remote Similarity	NPD4582	Approved
0.6569	Remote Similarity	NPD4583	Approved
0.6568	Remote Similarity	NPD3145	Approved
0.6568	Remote Similarity	NPD3144	Approved
0.6564	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7038	Approved
0.6562	Remote Similarity	NPD7039	Approved
0.6559	Remote Similarity	NPD4666	Phase 3
0.655	Remote Similarity	NPD2973	Approved
0.655	Remote Similarity	NPD2974	Approved
0.655	Remote Similarity	NPD2975	Approved
0.6548	Remote Similarity	NPD2488	Approved
0.6548	Remote Similarity	NPD2490	Approved
0.6543	Remote Similarity	NPD1357	Approved
0.6536	Remote Similarity	NPD6090	Discontinued
0.6535	Remote Similarity	NPD4580	Approved
0.6532	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD1753	Discontinued
0.6531	Remote Similarity	NPD3398	Discontinued
0.6527	Remote Similarity	NPD9619	Approved
0.6527	Remote Similarity	NPD9620	Approved
0.6527	Remote Similarity	NPD9621	Approved
0.652	Remote Similarity	NPD4004	Approved
0.652	Remote Similarity	NPD4002	Approved
0.6519	Remote Similarity	NPD4017	Approved
0.6514	Remote Similarity	NPD7037	Approved
0.6512	Remote Similarity	NPD2492	Phase 1
0.6512	Remote Similarity	NPD5314	Approved
0.6509	Remote Similarity	NPD3179	Approved
0.6509	Remote Similarity	NPD3180	Approved
0.6505	Remote Similarity	NPD5709	Phase 3
0.6503	Remote Similarity	NPD37	Approved
0.6503	Remote Similarity	NPD2668	Approved
0.6503	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD2667	Approved
0.65	Remote Similarity	NPD6031	Approved
0.65	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6030	Approved
0.65	Remote Similarity	NPD5976	Discontinued
0.65	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD8156	Discontinued
0.6492	Remote Similarity	NPD5312	Approved
0.6492	Remote Similarity	NPD5313	Approved
0.6489	Remote Similarity	NPD4166	Phase 2
0.6486	Remote Similarity	NPD4967	Phase 2
0.6486	Remote Similarity	NPD4965	Approved
0.6486	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4966	Approved
0.648	Remote Similarity	NPD4739	Approved
0.6471	Remote Similarity	NPD2972	Approved
0.6471	Remote Similarity	NPD3533	Approved
0.6471	Remote Similarity	NPD3057	Approved
0.6471	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5718	Phase 2
0.6467	Remote Similarity	NPD4585	Approved
0.6465	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD6667	Approved
0.6461	Remote Similarity	NPD6666	Approved
0.6461	Remote Similarity	NPD3122	Phase 3
0.6459	Remote Similarity	NPD5676	Approved
0.6457	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4055	Discovery
0.6448	Remote Similarity	NPD5090	Approved
0.6448	Remote Similarity	NPD5089	Approved
0.6448	Remote Similarity	NPD7110	Phase 1
0.6448	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6331	Phase 2
0.644	Remote Similarity	NPD8251	Approved
0.644	Remote Similarity	NPD8252	Approved
0.644	Remote Similarity	NPD8099	Discontinued
0.6435	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD3163	Approved
0.6433	Remote Similarity	NPD3162	Approved
0.6429	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD6297	Approved
0.6417	Remote Similarity	NPD6234	Discontinued
0.6417	Remote Similarity	NPD6315	Phase 2
0.6416	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7047	Phase 3
0.6413	Remote Similarity	NPD3382	Approved
0.6413	Remote Similarity	NPD3383	Approved
0.6413	Remote Similarity	NPD3384	Approved
0.6412	Remote Similarity	NPD3027	Phase 3
0.641	Remote Similarity	NPD2971	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