NPASS Compound

Structure

NPC263212 OpenBabel07101718322D 37 41 0 0 1 0 0 0 0 0999 V2000 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9791 3.0719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8801 2.6381 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1861 0.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1833 0.3475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6479 0.8765 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 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6228 2.9010 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6228 1.0990 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 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -3.0567 2.0000 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 -1.6479 3.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 1 0 0 0 0 0 0 0 0 0 -4.6172 1.2485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 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 -4.0539 2.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4253 4.0984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6144 1.3232 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 30 1 0 0 0 0 4 30 1 0 0 0 0 5 35 1 0 0 0 0 6 8 2 0 0 0 0 6 17 1 0 0 0 0 7 9 2 0 0 0 0 7 16 1 0 0 0 0 8 22 1 0 0 0 0 9 26 1 0 0 0 0 10 16 2 0 0 0 0 10 20 1 0 0 0 0 11 17 2 0 0 0 0 11 24 1 0 0 0 0 12 18 2 0 0 0 0 12 19 1 0 0 0 0 13 21 2 0 0 0 0 13 23 1 0 0 0 0 14 31 1 0 0 0 0 15 18 1 0 0 0 0 16 21 1 0 0 0 0 18 28 1 0 0 0 0 19 20 2 0 0 0 0 19 23 1 0 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 22 24 2 0 0 0 0 22 32 1 0 0 0 0 23 33 2 0 0 0 0 24 35 1 0 0 0 0 25 14 1 6 0 0 0 25 27 1 0 0 0 0 25 36 1 0 0 0 0 26 30 1 0 0 0 0 26 34 2 0 0 0 0 27 17 1 1 0 0 0 27 37 1 0 0 0 0 28 29 2 0 0 0 0 28 37 1 0 0 0 0 29 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.2
Volume:	517.184
LogP:	4.92
LogD:	3.417
LogS:	-4.801
# Rotatable Bonds:	4
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.529
Synthetic Accessibility Score:	4.058
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.889
MDCK Permeability:	2.877399128919933e-05
Pgp-inhibitor:	0.979
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.062

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.087
Plasma Protein Binding (PPB):	96.0644760131836%
Volume Distribution (VD):	0.558
Pgp-substrate:	7.045623779296875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.087
CYP1A2-substrate:	0.86
CYP2C19-inhibitor:	0.462
CYP2C19-substrate:	0.756
CYP2C9-inhibitor:	0.885
CYP2C9-substrate:	0.821
CYP2D6-inhibitor:	0.451
CYP2D6-substrate:	0.273
CYP3A4-inhibitor:	0.737
CYP3A4-substrate:	0.911

ADMET: Excretion

Clearance (CL):	1.504
Half-life (T1/2):	0.11

ADMET: Toxicity

hERG Blockers:	0.248
Human Hepatotoxicity (H-HT):	0.341
Drug-inuced Liver Injury (DILI):	0.869
AMES Toxicity:	0.12
Rat Oral Acute Toxicity:	0.774
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.947
Carcinogencity:	0.546
Eye Corrosion:	0.003
Eye Irritation:	0.314
Respiratory Toxicity:	0.15

Download Data

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

Natural Product: NPC263212

Natural Product ID:	NPC263212
*Common Name:**	Brevitaxin
IUPAC Name:	n.a.
Synonyms:	Brevitaxin
Standard InCHIKey:	STCQKVIMCUPRKK-BDYUSTAISA-N
Standard InCHI:	InChI=1S/C30H30O7/c1-15(2)18-12-19-20(10-16-7-9-26(34)30(3,4)21(16)13-23(19)33)29-28(18)37-27(25(14-31)36-29)17-6-8-22(32)24(11-17)35-5/h6-13,15,25,27,31-32H,14H2,1-5H3/t25-,27-/m0/s1
SMILES:	OC[C@@H]1Oc2c(O[C@H]1c1ccc(c(c1)OC)O)c(cc1c2cc2C=CC(=O)C(c2cc1=O)(C)C)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485660
PubChem CID:	10074772
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1955887]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2878063]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7130988]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	bark	n.a.	n.a.	PMID[7623034]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27064	Taxus brevifolia	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27064	Taxus brevifolia	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT90	Cell Line	DU-145	Homo sapiens	ED50	=	6.8	uM	PMID[521280]

☑ 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 NPC263212 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	440
0.1-0.2	1582
0.2-0.3	3252
0.3-0.4	8405
0.4-0.5	10229
0.5-0.6	3666
0.6-0.7	5744
0.7-0.8	7798
0.8-0.85	1492
0.85-0.9	88
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8988	High Similarity	NPC475054
0.8938	High Similarity	NPC180901
0.8938	High Similarity	NPC300757
0.8909	High Similarity	NPC43319
0.8869	High Similarity	NPC199357
0.8855	High Similarity	NPC474024
0.8855	High Similarity	NPC218226
0.8848	High Similarity	NPC472277
0.8834	High Similarity	NPC36217
0.8834	High Similarity	NPC472962
0.8834	High Similarity	NPC472961
0.8824	High Similarity	NPC47191
0.8812	High Similarity	NPC131121
0.8802	High Similarity	NPC288813
0.8788	High Similarity	NPC205265
0.8788	High Similarity	NPC220313
0.8788	High Similarity	NPC18100
0.8788	High Similarity	NPC186686
0.8788	High Similarity	NPC476295
0.8788	High Similarity	NPC472281
0.8773	High Similarity	NPC85121
0.8773	High Similarity	NPC235448
0.8758	High Similarity	NPC62051
0.8743	High Similarity	NPC117854
0.8743	High Similarity	NPC6588
0.8743	High Similarity	NPC477154
0.8735	High Similarity	NPC25361
0.8735	High Similarity	NPC303174
0.8735	High Similarity	NPC293319
0.8727	High Similarity	NPC201800
0.8727	High Similarity	NPC474150
0.8727	High Similarity	NPC474162
0.8727	High Similarity	NPC472964
0.8727	High Similarity	NPC476247
0.8727	High Similarity	NPC474034
0.8727	High Similarity	NPC474033
0.8727	High Similarity	NPC470694
0.872	High Similarity	NPC321399
0.872	High Similarity	NPC472902
0.8712	High Similarity	NPC299520
0.8712	High Similarity	NPC219867
0.8712	High Similarity	NPC296044
0.8712	High Similarity	NPC161960
0.8712	High Similarity	NPC472598
0.8712	High Similarity	NPC129684
0.8712	High Similarity	NPC474055
0.8712	High Similarity	NPC180011
0.8712	High Similarity	NPC187745
0.8712	High Similarity	NPC291508
0.8712	High Similarity	NPC304008
0.8712	High Similarity	NPC167098
0.8698	High Similarity	NPC4200
0.8698	High Similarity	NPC472620
0.869	High Similarity	NPC188079
0.8688	High Similarity	NPC475718
0.8683	High Similarity	NPC272502
0.8683	High Similarity	NPC477517
0.8683	High Similarity	NPC37870
0.8679	High Similarity	NPC98809
0.8679	High Similarity	NPC476394
0.8675	High Similarity	NPC236132
0.8675	High Similarity	NPC7483
0.8675	High Similarity	NPC124038
0.8675	High Similarity	NPC197168
0.8667	High Similarity	NPC472275
0.8667	High Similarity	NPC234644
0.8667	High Similarity	NPC472632
0.8667	High Similarity	NPC474038
0.8667	High Similarity	NPC26326
0.8667	High Similarity	NPC57715
0.8667	High Similarity	NPC32694
0.8667	High Similarity	NPC134783
0.8667	High Similarity	NPC472906
0.8663	High Similarity	NPC212290
0.8662	High Similarity	NPC309169
0.8662	High Similarity	NPC196941
0.8659	High Similarity	NPC197856
0.8659	High Similarity	NPC210459
0.865	High Similarity	NPC115853
0.865	High Similarity	NPC478223
0.865	High Similarity	NPC288353
0.865	High Similarity	NPC291878
0.865	High Similarity	NPC35038
0.865	High Similarity	NPC195796
0.865	High Similarity	NPC278778
0.8639	High Similarity	NPC472276
0.8634	High Similarity	NPC302783
0.8634	High Similarity	NPC124842
0.8634	High Similarity	NPC473201
0.8634	High Similarity	NPC144283
0.8625	High Similarity	NPC303989
0.8625	High Similarity	NPC472837
0.8623	High Similarity	NPC62261
0.8623	High Similarity	NPC326520
0.8623	High Similarity	NPC475888
0.8623	High Similarity	NPC472450
0.8623	High Similarity	NPC275780
0.8623	High Similarity	NPC239752
0.8623	High Similarity	NPC26386
0.8623	High Similarity	NPC473286
0.8616	High Similarity	NPC52692
0.8614	High Similarity	NPC211107
0.8608	High Similarity	NPC287495
0.8608	High Similarity	NPC9370
0.8606	High Similarity	NPC475784
0.8606	High Similarity	NPC45146
0.8606	High Similarity	NPC299436
0.8606	High Similarity	NPC471973
0.8606	High Similarity	NPC228785
0.8606	High Similarity	NPC174953
0.8606	High Similarity	NPC474960
0.8606	High Similarity	NPC24627
0.8606	High Similarity	NPC282009
0.8606	High Similarity	NPC192686
0.8606	High Similarity	NPC119209
0.8606	High Similarity	NPC14353
0.8606	High Similarity	NPC287328
0.8606	High Similarity	NPC235018
0.8606	High Similarity	NPC56085
0.8606	High Similarity	NPC188433
0.8606	High Similarity	NPC297212
0.8606	High Similarity	NPC118256
0.8599	High Similarity	NPC50954
0.8598	High Similarity	NPC136674
0.8598	High Similarity	NPC27337
0.8596	High Similarity	NPC294149
0.8589	High Similarity	NPC152951
0.8589	High Similarity	NPC168247
0.8589	High Similarity	NPC31018
0.8589	High Similarity	NPC117992
0.8589	High Similarity	NPC230149
0.8589	High Similarity	NPC255807
0.8589	High Similarity	NPC478159
0.8589	High Similarity	NPC321779
0.8589	High Similarity	NPC45849
0.8589	High Similarity	NPC200761
0.8589	High Similarity	NPC477503
0.8589	High Similarity	NPC57674
0.8589	High Similarity	NPC478161
0.8589	High Similarity	NPC67396
0.8589	High Similarity	NPC470327
0.858	High Similarity	NPC164912
0.858	High Similarity	NPC300307
0.858	High Similarity	NPC180388
0.858	High Similarity	NPC472619
0.858	High Similarity	NPC476637
0.8571	High Similarity	NPC13481
0.8571	High Similarity	NPC39091
0.8571	High Similarity	NPC170245
0.8571	High Similarity	NPC43065
0.8571	High Similarity	NPC128293
0.8571	High Similarity	NPC235610
0.8571	High Similarity	NPC207575
0.8563	High Similarity	NPC472278
0.8563	High Similarity	NPC472625
0.8563	High Similarity	NPC236521
0.8563	High Similarity	NPC207690
0.8563	High Similarity	NPC319200
0.8563	High Similarity	NPC474240
0.8563	High Similarity	NPC473313
0.8563	High Similarity	NPC228209
0.8563	High Similarity	NPC189473
0.8563	High Similarity	NPC270837
0.8563	High Similarity	NPC329669
0.8563	High Similarity	NPC45943
0.8563	High Similarity	NPC152659
0.8563	High Similarity	NPC303460
0.8563	High Similarity	NPC12461
0.8563	High Similarity	NPC248638
0.8563	High Similarity	NPC306321
0.8563	High Similarity	NPC23298
0.8563	High Similarity	NPC187491
0.8562	High Similarity	NPC474556
0.8554	High Similarity	NPC266314
0.8554	High Similarity	NPC474187
0.8554	High Similarity	NPC471210
0.8554	High Similarity	NPC474186
0.8554	High Similarity	NPC61010
0.8554	High Similarity	NPC142252
0.8554	High Similarity	NPC40491
0.8554	High Similarity	NPC471499
0.8554	High Similarity	NPC469889
0.8554	High Similarity	NPC278052
0.8554	High Similarity	NPC472634
0.8545	High Similarity	NPC95936
0.8545	High Similarity	NPC329091
0.8545	High Similarity	NPC22192
0.8545	High Similarity	NPC53545
0.8545	High Similarity	NPC172770
0.8545	High Similarity	NPC117418
0.8545	High Similarity	NPC473990
0.8545	High Similarity	NPC46736
0.8545	High Similarity	NPC104876
0.8545	High Similarity	NPC204879
0.8545	High Similarity	NPC100123
0.8545	High Similarity	NPC250214
0.8545	High Similarity	NPC245891
0.8545	High Similarity	NPC185258
0.8538	High Similarity	NPC471969
0.8538	High Similarity	NPC316539

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 NPC263212 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	387
0.1-0.2	927
0.2-0.3	1701
0.3-0.4	2613
0.4-0.5	1902
0.5-0.6	960
0.6-0.7	494
0.7-0.8	149
0.8-0.85	16
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.858	High Similarity	NPD5844	Phase 1
0.8528	High Similarity	NPD2393	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD1934	Approved
0.8313	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD6166	Phase 2
0.8294	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD5494	Approved
0.8239	Intermediate Similarity	NPD4628	Phase 3
0.8193	Intermediate Similarity	NPD2801	Approved
0.8161	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD7473	Discontinued
0.8136	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD4380	Phase 2
0.8103	Intermediate Similarity	NPD7074	Phase 3
0.8101	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD3882	Suspended
0.8092	Intermediate Similarity	NPD3818	Discontinued
0.8084	Intermediate Similarity	NPD1465	Phase 2
0.807	Intermediate Similarity	NPD6232	Discontinued
0.8046	Intermediate Similarity	NPD7054	Approved
0.8012	Intermediate Similarity	NPD6959	Discontinued
0.8	Intermediate Similarity	NPD7472	Approved
0.7921	Intermediate Similarity	NPD8312	Approved
0.7921	Intermediate Similarity	NPD8313	Approved
0.787	Intermediate Similarity	NPD7819	Suspended
0.7866	Intermediate Similarity	NPD1511	Approved
0.7865	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6797	Phase 2
0.7844	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7075	Discontinued
0.7836	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD7251	Discontinued
0.7771	Intermediate Similarity	NPD1512	Approved
0.7765	Intermediate Similarity	NPD7808	Phase 3
0.7765	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD7458	Discontinued
0.7738	Intermediate Similarity	NPD3226	Approved
0.773	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD3817	Phase 2
0.7717	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD2346	Discontinued
0.7711	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD6559	Discontinued
0.7709	Intermediate Similarity	NPD7685	Pre-registration
0.7701	Intermediate Similarity	NPD8127	Discontinued
0.7692	Intermediate Similarity	NPD8434	Phase 2
0.7692	Intermediate Similarity	NPD6599	Discontinued
0.7692	Intermediate Similarity	NPD8150	Discontinued
0.7688	Intermediate Similarity	NPD6234	Discontinued
0.7684	Intermediate Similarity	NPD7228	Approved
0.7683	Intermediate Similarity	NPD3750	Approved
0.7669	Intermediate Similarity	NPD1549	Phase 2
0.7665	Intermediate Similarity	NPD6273	Approved
0.7654	Intermediate Similarity	NPD6100	Approved
0.7654	Intermediate Similarity	NPD6099	Approved
0.764	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6674	Discontinued
0.7607	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD37	Approved
0.7602	Intermediate Similarity	NPD6801	Discontinued
0.7584	Intermediate Similarity	NPD3751	Discontinued
0.7576	Intermediate Similarity	NPD7003	Approved
0.7576	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD8166	Discontinued
0.7572	Intermediate Similarity	NPD4966	Approved
0.7572	Intermediate Similarity	NPD4965	Approved
0.7572	Intermediate Similarity	NPD4967	Phase 2
0.7562	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1613	Approved
0.7544	Intermediate Similarity	NPD7411	Suspended
0.7515	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2533	Approved
0.7485	Intermediate Similarity	NPD2799	Discontinued
0.7468	Intermediate Similarity	NPD9494	Approved
0.7448	Intermediate Similarity	NPD2491	Approved
0.7448	Intermediate Similarity	NPD3057	Approved
0.7439	Intermediate Similarity	NPD2796	Approved
0.7435	Intermediate Similarity	NPD6777	Approved
0.7435	Intermediate Similarity	NPD6779	Approved
0.7435	Intermediate Similarity	NPD6780	Approved
0.7435	Intermediate Similarity	NPD6776	Approved
0.7435	Intermediate Similarity	NPD6781	Approved
0.7435	Intermediate Similarity	NPD6782	Approved
0.7435	Intermediate Similarity	NPD6778	Approved
0.7432	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6190	Approved
0.7414	Intermediate Similarity	NPD5402	Approved
0.741	Intermediate Similarity	NPD2800	Approved
0.7396	Intermediate Similarity	NPD2494	Approved
0.7396	Intermediate Similarity	NPD2493	Approved
0.738	Intermediate Similarity	NPD2490	Approved
0.738	Intermediate Similarity	NPD2488	Approved
0.7378	Intermediate Similarity	NPD3748	Approved
0.7378	Intermediate Similarity	NPD1510	Phase 2
0.7375	Intermediate Similarity	NPD3027	Phase 3
0.7374	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD4583	Approved
0.7371	Intermediate Similarity	NPD4582	Approved
0.7362	Intermediate Similarity	NPD1607	Approved
0.736	Intermediate Similarity	NPD3787	Discontinued
0.7358	Intermediate Similarity	NPD3533	Approved
0.7358	Intermediate Similarity	NPD2972	Approved
0.7358	Intermediate Similarity	NPD3448	Approved
0.7346	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD4060	Phase 1
0.7346	Intermediate Similarity	NPD3620	Phase 2
0.7344	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6799	Approved
0.7333	Intermediate Similarity	NPD2935	Discontinued
0.733	Intermediate Similarity	NPD3749	Approved
0.7327	Intermediate Similarity	NPD4111	Phase 1
0.7327	Intermediate Similarity	NPD4665	Approved
0.7325	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7435	Discontinued
0.732	Intermediate Similarity	NPD4002	Approved
0.732	Intermediate Similarity	NPD4004	Approved
0.7318	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD3452	Approved
0.7306	Intermediate Similarity	NPD3450	Approved
0.7303	Intermediate Similarity	NPD1247	Approved
0.7301	Intermediate Similarity	NPD230	Phase 1
0.7293	Intermediate Similarity	NPD7177	Discontinued
0.7273	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7768	Phase 2
0.7262	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4110	Phase 3
0.7261	Intermediate Similarity	NPD3972	Approved
0.7257	Intermediate Similarity	NPD8455	Phase 2
0.7257	Intermediate Similarity	NPD5761	Phase 2
0.7257	Intermediate Similarity	NPD5760	Phase 2
0.725	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1240	Approved
0.7239	Intermediate Similarity	NPD943	Approved
0.7231	Intermediate Similarity	NPD7697	Approved
0.7231	Intermediate Similarity	NPD7698	Approved
0.7231	Intermediate Similarity	NPD7696	Phase 3
0.7228	Intermediate Similarity	NPD7240	Approved
0.7222	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3926	Phase 2
0.7222	Intermediate Similarity	NPD8151	Discontinued
0.7209	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5403	Approved
0.7195	Intermediate Similarity	NPD447	Suspended
0.7194	Intermediate Similarity	NPD7871	Phase 2
0.7194	Intermediate Similarity	NPD7870	Phase 2
0.7191	Intermediate Similarity	NPD919	Approved
0.7188	Intermediate Similarity	NPD2973	Approved
0.7188	Intermediate Similarity	NPD2975	Approved
0.7188	Intermediate Similarity	NPD2974	Approved
0.7186	Intermediate Similarity	NPD7266	Discontinued
0.7186	Intermediate Similarity	NPD2344	Approved
0.7184	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7028	Phase 2
0.7182	Intermediate Similarity	NPD2489	Approved
0.7182	Intermediate Similarity	NPD27	Approved
0.7179	Intermediate Similarity	NPD6823	Phase 2
0.7173	Intermediate Similarity	NPD6534	Approved
0.7173	Intermediate Similarity	NPD6535	Approved
0.7172	Intermediate Similarity	NPD7701	Phase 2
0.7171	Intermediate Similarity	NPD7907	Approved
0.7168	Intermediate Similarity	NPD1653	Approved
0.7165	Intermediate Similarity	NPD4580	Approved
0.716	Intermediate Similarity	NPD4625	Phase 3
0.715	Intermediate Similarity	NPD7783	Phase 2
0.715	Intermediate Similarity	NPD7801	Approved
0.715	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5676	Approved
0.7143	Intermediate Similarity	NPD2424	Discontinued
0.7143	Intermediate Similarity	NPD2861	Phase 2
0.7135	Intermediate Similarity	NPD7390	Discontinued
0.7135	Intermediate Similarity	NPD7038	Approved
0.7135	Intermediate Similarity	NPD7039	Approved
0.7127	Intermediate Similarity	NPD2969	Approved
0.7127	Intermediate Similarity	NPD2970	Approved
0.7126	Intermediate Similarity	NPD2438	Suspended
0.7117	Intermediate Similarity	NPD2313	Discontinued
0.71	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7874	Approved
0.7099	Intermediate Similarity	NPD4908	Phase 1
0.7093	Intermediate Similarity	NPD5401	Approved
0.7091	Intermediate Similarity	NPD6355	Discontinued
0.7083	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3823	Discontinued
0.7077	Intermediate Similarity	NPD4107	Approved
0.7072	Intermediate Similarity	NPD5711	Approved
0.7072	Intermediate Similarity	NPD5710	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