NPASS Compound

Structure

CID231945 OpenBabel06191716032D 33 37 0 0 1 0 0 0 0 0999 V2000 3.4478 -1.4216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9556 -0.5703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6739 3.7101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2309 2.9431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4653 -0.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0241 -1.9121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0239 0.9629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6438 -2.8453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6434 -0.9494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8214 -1.4236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1083 1.4216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6442 1.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4649 -2.3706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8222 -2.3716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1081 0.4733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8222 1.4226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2878 1.8963 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4659 1.4221 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6436 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9489 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6425 0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6428 -0.9484 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8211 0.4747 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4644 -1.4222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2881 2.8443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4656 0.4738 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8216 -1.4231 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8220 0.4742 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4855 0.4875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8208 1.4483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4222 3.2301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 29 1 0 0 0 0 9 14 1 0 0 0 0 9 15 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 17 1 0 0 0 0 13 19 1 0 0 0 0 14 25 1 0 0 0 0 15 28 1 0 0 0 0 16 27 1 0 0 0 0 17 29 1 0 0 0 0 18 19 1 0 0 0 0 18 26 1 6 0 0 0 19 27 1 6 0 0 0 20 27 1 6 0 0 0 20 29 1 0 0 0 0 21 28 1 1 0 0 0 21 30 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 22 31 1 1 0 0 0 23 25 1 0 0 0 0 23 28 1 1 0 0 0 24 30 1 1 0 0 0 24 32 1 0 0 0 0 26 33 1 0 0 0 0 27 5 1 6 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.39
Volume:	511.024
LogP:	5.779
LogD:	5.049
LogS:	-4.822
# Rotatable Bonds:	1
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.437
Synthetic Accessibility Score:	5.007
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.838
MDCK Permeability:	1.595947651367169e-05
Pgp-inhibitor:	0.858
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.946
30% Bioavailability (F30%):	0.886

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	95.20211791992188%
Volume Distribution (VD):	1.026
Pgp-substrate:	2.006584882736206%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.22
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.923
CYP2C9-inhibitor:	0.141
CYP2C9-substrate:	0.377
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.382
CYP3A4-inhibitor:	0.255
CYP3A4-substrate:	0.215

ADMET: Excretion

Clearance (CL):	4.812
Half-life (T1/2):	0.084

ADMET: Toxicity

hERG Blockers:	0.364
Human Hepatotoxicity (H-HT):	0.13
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.183
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.809
Carcinogencity:	0.018
Eye Corrosion:	0.311
Eye Irritation:	0.055
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC231945

Natural Product ID:	NPC231945
*Common Name:**	Hopane-6Beta,7Beta,22-Triol
IUPAC Name:	(3S,3aS,5aR,5bR,6R,7S,7aS,11aR,11bR,13aR,13bS)-3-(2-hydroxypropan-2-yl)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysene-6,7-diol
Synonyms:	Hopane-6Beta,7Beta,22-Triol
Standard InCHIKey:	VYLJAYXZTOTZRR-QKJSLZMYSA-N
Standard InCHI:	InChI=1S/C30H52O3/c1-25(2)14-9-15-28(6)21-11-10-20-27(5)16-12-18(26(3,4)33)19(27)13-17-29(20,7)30(21,8)24(32)22(31)23(25)28/h18-24,31-33H,9-17H2,1-8H3/t18-,19-,20+,21+,22-,23-,24-,27-,28+,29+,30-/m0/s1
SMILES:	CC1(C)CCC[C@]2(C)[C@H]3CC[C@@H]4[C@@]5(C)CC[C@@H]([C@@H]5CC[C@@]4(C)[C@]3(C)[C@H]([C@H]([C@@H]12)O)O)C(C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1774510
PubChem CID:	52951751
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001823] Hopanoids

*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
NPO21470	Conoideocrella tenuis	Species	Clavicipitaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21473608]
NPO32716	conoideocrella tenuis bcc 18627	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21473608]
NPO21470	Conoideocrella tenuis	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21473608]
NPO21470	Conoideocrella tenuis	Species	Clavicipitaceae	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	6
MIC	1

Activity Type	# Activity
Cell Line	4
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	109000.0	nM	PMID[575301]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	109000.0	nM	PMID[575301]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	>	109000.0	nM	PMID[575301]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	109000.0	nM	PMID[575301]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	>	22000.0	nM	PMID[575301]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	>	109000.0	nM	PMID[575301]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	IC50	>	109000.0	nM	PMID[575301]

☑ 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 NPC231945 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	405
0.1-0.2	4794
0.2-0.3	16989
0.3-0.4	8999
0.4-0.5	4425
0.5-0.6	4103
0.6-0.7	2208
0.7-0.8	611
0.8-0.85	102
0.85-0.9	43
0.9-0.95	15
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9538	High Similarity	NPC48079
0.9394	High Similarity	NPC472741
0.9385	High Similarity	NPC142712
0.9254	High Similarity	NPC254037
0.9254	High Similarity	NPC241085
0.9254	High Similarity	NPC107919
0.9254	High Similarity	NPC299948
0.9254	High Similarity	NPC470830
0.9254	High Similarity	NPC129829
0.9231	High Similarity	NPC260116
0.9118	High Similarity	NPC192192
0.9104	High Similarity	NPC475893
0.9	High Similarity	NPC228994
0.9	High Similarity	NPC10476
0.9	High Similarity	NPC192501
0.8986	High Similarity	NPC127094
0.8955	High Similarity	NPC63190
0.8955	High Similarity	NPC204233
0.8923	High Similarity	NPC114891
0.8873	High Similarity	NPC243027
0.8873	High Similarity	NPC158208
0.8873	High Similarity	NPC196136
0.8857	High Similarity	NPC153719
0.8857	High Similarity	NPC472341
0.8857	High Similarity	NPC473238
0.8841	High Similarity	NPC282454
0.8769	High Similarity	NPC148174
0.8769	High Similarity	NPC71460
0.8769	High Similarity	NPC218585
0.8767	High Similarity	NPC102708
0.875	High Similarity	NPC163597
0.8732	High Similarity	NPC477508
0.8714	High Similarity	NPC473279
0.8714	High Similarity	NPC157422
0.8714	High Similarity	NPC100586
0.8714	High Similarity	NPC109457
0.8714	High Similarity	NPC157777
0.8714	High Similarity	NPC131506
0.8696	High Similarity	NPC66407
0.8696	High Similarity	NPC99264
0.8676	High Similarity	NPC473230
0.8676	High Similarity	NPC475884
0.8657	High Similarity	NPC473276
0.8657	High Similarity	NPC80463
0.8657	High Similarity	NPC475943
0.8657	High Similarity	NPC243469
0.8657	High Similarity	NPC474380
0.8657	High Similarity	NPC190827
0.8657	High Similarity	NPC41577
0.863	High Similarity	NPC128951
0.863	High Similarity	NPC192046
0.863	High Similarity	NPC302578
0.863	High Similarity	NPC105208
0.863	High Similarity	NPC477227
0.8611	High Similarity	NPC317242
0.8611	High Similarity	NPC270306
0.8611	High Similarity	NPC91387
0.8611	High Similarity	NPC231680
0.8592	High Similarity	NPC470610
0.8529	High Similarity	NPC44122
0.8514	High Similarity	NPC67657
0.8514	High Similarity	NPC18857
0.8514	High Similarity	NPC147993
0.8507	High Similarity	NPC159654
0.8507	High Similarity	NPC167995
0.8507	High Similarity	NPC69149
0.8507	High Similarity	NPC281540
0.8507	High Similarity	NPC118937
0.8493	Intermediate Similarity	NPC473916
0.8493	Intermediate Similarity	NPC470145
0.8493	Intermediate Similarity	NPC477602
0.8493	Intermediate Similarity	NPC477601
0.8493	Intermediate Similarity	NPC91573
0.8472	Intermediate Similarity	NPC48795
0.8451	Intermediate Similarity	NPC8004
0.8451	Intermediate Similarity	NPC1340
0.8451	Intermediate Similarity	NPC187471
0.8451	Intermediate Similarity	NPC195530
0.8451	Intermediate Similarity	NPC470071
0.8451	Intermediate Similarity	NPC252182
0.8451	Intermediate Similarity	NPC127283
0.8429	Intermediate Similarity	NPC470833
0.8429	Intermediate Similarity	NPC477820
0.8382	Intermediate Similarity	NPC472946
0.8378	Intermediate Similarity	NPC185915
0.8378	Intermediate Similarity	NPC133596
0.8378	Intermediate Similarity	NPC474574
0.8378	Intermediate Similarity	NPC11907
0.8378	Intermediate Similarity	NPC23884
0.8378	Intermediate Similarity	NPC64081
0.8358	Intermediate Similarity	NPC292419
0.8358	Intermediate Similarity	NPC290791
0.8356	Intermediate Similarity	NPC212879
0.8356	Intermediate Similarity	NPC231256
0.8356	Intermediate Similarity	NPC104387
0.8356	Intermediate Similarity	NPC174964
0.8356	Intermediate Similarity	NPC97534
0.8356	Intermediate Similarity	NPC195155
0.8356	Intermediate Similarity	NPC240235
0.8356	Intermediate Similarity	NPC178383
0.831	Intermediate Similarity	NPC251201
0.831	Intermediate Similarity	NPC63588
0.831	Intermediate Similarity	NPC232925
0.8308	Intermediate Similarity	NPC162685
0.8308	Intermediate Similarity	NPC476735
0.8289	Intermediate Similarity	NPC16449
0.8267	Intermediate Similarity	NPC42853
0.8243	Intermediate Similarity	NPC14112
0.8243	Intermediate Similarity	NPC78067
0.8243	Intermediate Similarity	NPC475742
0.8243	Intermediate Similarity	NPC278091
0.8243	Intermediate Similarity	NPC93662
0.8243	Intermediate Similarity	NPC86305
0.8243	Intermediate Similarity	NPC5767
0.8219	Intermediate Similarity	NPC25511
0.8219	Intermediate Similarity	NPC192638
0.8219	Intermediate Similarity	NPC62657
0.8219	Intermediate Similarity	NPC304499
0.8194	Intermediate Similarity	NPC478103
0.8158	Intermediate Similarity	NPC287452
0.8158	Intermediate Similarity	NPC81074
0.8158	Intermediate Similarity	NPC477282
0.8158	Intermediate Similarity	NPC220379
0.8158	Intermediate Similarity	NPC49627
0.8158	Intermediate Similarity	NPC49599
0.8154	Intermediate Similarity	NPC135438
0.8133	Intermediate Similarity	NPC221420
0.8133	Intermediate Similarity	NPC212241
0.8133	Intermediate Similarity	NPC202540
0.8133	Intermediate Similarity	NPC298168
0.8133	Intermediate Similarity	NPC248830
0.8133	Intermediate Similarity	NPC119355
0.8133	Intermediate Similarity	NPC143133
0.8108	Intermediate Similarity	NPC3403
0.8082	Intermediate Similarity	NPC253805
0.8082	Intermediate Similarity	NPC232112
0.8082	Intermediate Similarity	NPC81759
0.8077	Intermediate Similarity	NPC202688
0.8077	Intermediate Similarity	NPC60018
0.8077	Intermediate Similarity	NPC154043
0.8052	Intermediate Similarity	NPC13554
0.803	Intermediate Similarity	NPC47663
0.8028	Intermediate Similarity	NPC469987
0.8028	Intermediate Similarity	NPC474756
0.7975	Intermediate Similarity	NPC207013
0.7975	Intermediate Similarity	NPC216420
0.7975	Intermediate Similarity	NPC85095
0.7975	Intermediate Similarity	NPC478054
0.7975	Intermediate Similarity	NPC211135
0.7973	Intermediate Similarity	NPC478130
0.7949	Intermediate Similarity	NPC12933
0.7949	Intermediate Similarity	NPC109533
0.7949	Intermediate Similarity	NPC73515
0.7945	Intermediate Similarity	NPC156277
0.7945	Intermediate Similarity	NPC111234
0.7945	Intermediate Similarity	NPC320549
0.7945	Intermediate Similarity	NPC151018
0.7945	Intermediate Similarity	NPC58057
0.7941	Intermediate Similarity	NPC185547
0.7941	Intermediate Similarity	NPC95804
0.7922	Intermediate Similarity	NPC80297
0.7922	Intermediate Similarity	NPC269333
0.7922	Intermediate Similarity	NPC116119
0.7922	Intermediate Similarity	NPC472742
0.7922	Intermediate Similarity	NPC475727
0.791	Intermediate Similarity	NPC95958
0.7895	Intermediate Similarity	NPC475031
0.7895	Intermediate Similarity	NPC476233
0.7895	Intermediate Similarity	NPC171658
0.7887	Intermediate Similarity	NPC475172
0.7879	Intermediate Similarity	NPC236588
0.7875	Intermediate Similarity	NPC320824
0.7867	Intermediate Similarity	NPC70982
0.7867	Intermediate Similarity	NPC273366
0.7867	Intermediate Similarity	NPC212733
0.7867	Intermediate Similarity	NPC185536
0.7867	Intermediate Similarity	NPC230704
0.7848	Intermediate Similarity	NPC475388
0.7848	Intermediate Similarity	NPC268040
0.7848	Intermediate Similarity	NPC477599
0.7848	Intermediate Similarity	NPC121121
0.7826	Intermediate Similarity	NPC249078
0.7826	Intermediate Similarity	NPC209686
0.7826	Intermediate Similarity	NPC236099
0.7821	Intermediate Similarity	NPC236112
0.7821	Intermediate Similarity	NPC22403
0.7821	Intermediate Similarity	NPC475679
0.7808	Intermediate Similarity	NPC45296
0.7792	Intermediate Similarity	NPC472342
0.7792	Intermediate Similarity	NPC471769
0.7792	Intermediate Similarity	NPC285761
0.7792	Intermediate Similarity	NPC301707
0.7792	Intermediate Similarity	NPC31828
0.7778	Intermediate Similarity	NPC273290
0.7778	Intermediate Similarity	NPC290612
0.7778	Intermediate Similarity	NPC232044
0.7778	Intermediate Similarity	NPC266651
0.7763	Intermediate Similarity	NPC472486
0.7763	Intermediate Similarity	NPC472487
0.7763	Intermediate Similarity	NPC4209

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 NPC231945 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	411
0.1-0.2	4510
0.2-0.3	3048
0.3-0.4	716
0.4-0.5	176
0.5-0.6	218
0.6-0.7	44
0.7-0.8	25
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9254	High Similarity	NPD4267	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD4787	Phase 1
0.7945	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD6117	Approved
0.7733	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6116	Phase 1
0.7595	Intermediate Similarity	NPD7525	Registered
0.7564	Intermediate Similarity	NPD6118	Approved
0.7564	Intermediate Similarity	NPD6114	Approved
0.7564	Intermediate Similarity	NPD6115	Approved
0.7564	Intermediate Similarity	NPD6697	Approved
0.7534	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD5360	Phase 3
0.7403	Intermediate Similarity	NPD3703	Phase 2
0.7375	Intermediate Similarity	NPD6928	Phase 2
0.7349	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4244	Approved
0.7333	Intermediate Similarity	NPD4789	Approved
0.7333	Intermediate Similarity	NPD4245	Approved
0.72	Intermediate Similarity	NPD3698	Phase 2
0.7123	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7645	Phase 2
0.7013	Intermediate Similarity	NPD4758	Discontinued
0.6962	Remote Similarity	NPD7339	Approved
0.6962	Remote Similarity	NPD6942	Approved
0.6914	Remote Similarity	NPD3671	Phase 1
0.6875	Remote Similarity	NPD6933	Approved
0.6842	Remote Similarity	NPD6705	Phase 1
0.6778	Remote Similarity	NPD8171	Discontinued
0.6757	Remote Similarity	NPD371	Approved
0.6747	Remote Similarity	NPD4748	Discontinued
0.6707	Remote Similarity	NPD5364	Discontinued
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD8035	Phase 2
0.6625	Remote Similarity	NPD6924	Approved
0.6625	Remote Similarity	NPD6926	Approved
0.6615	Remote Similarity	NPD385	Approved
0.6615	Remote Similarity	NPD384	Approved
0.6582	Remote Similarity	NPD6081	Approved
0.6579	Remote Similarity	NPD4224	Phase 2
0.6556	Remote Similarity	NPD6700	Approved
0.6556	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD3702	Approved
0.6512	Remote Similarity	NPD4788	Approved
0.6484	Remote Similarity	NPD6702	Approved
0.6484	Remote Similarity	NPD6703	Approved
0.6444	Remote Similarity	NPD5328	Approved
0.6437	Remote Similarity	NPD4786	Approved
0.6375	Remote Similarity	NPD4243	Approved
0.6375	Remote Similarity	NPD5777	Approved
0.6304	Remote Similarity	NPD6079	Approved
0.6292	Remote Similarity	NPD3618	Phase 1
0.6237	Remote Similarity	NPD4202	Approved
0.6222	Remote Similarity	NPD7524	Approved
0.6222	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.622	Remote Similarity	NPD4785	Approved
0.622	Remote Similarity	NPD4784	Approved
0.6207	Remote Similarity	NPD3667	Approved
0.6173	Remote Similarity	NPD7150	Approved
0.6173	Remote Similarity	NPD7151	Approved
0.6173	Remote Similarity	NPD7152	Approved
0.6163	Remote Similarity	NPD7509	Discontinued
0.6163	Remote Similarity	NPD6931	Approved
0.6163	Remote Similarity	NPD6930	Phase 2
0.6146	Remote Similarity	NPD7920	Phase 3
0.6146	Remote Similarity	NPD7919	Phase 3
0.6129	Remote Similarity	NPD7515	Phase 2
0.6125	Remote Similarity	NPD6923	Approved
0.6125	Remote Similarity	NPD6922	Approved
0.6122	Remote Similarity	NPD4159	Approved
0.6111	Remote Similarity	NPD8308	Discontinued
0.6105	Remote Similarity	NPD7991	Discontinued
0.61	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD8088	Phase 1
0.6049	Remote Similarity	NPD7143	Approved
0.6049	Remote Similarity	NPD7144	Approved
0.6047	Remote Similarity	NPD6929	Approved
0.602	Remote Similarity	NPD8418	Phase 2
0.6	Remote Similarity	NPD6932	Approved
0.5979	Remote Similarity	NPD4755	Approved
0.597	Remote Similarity	NPD388	Approved
0.597	Remote Similarity	NPD386	Approved
0.5955	Remote Similarity	NPD6695	Phase 3
0.5952	Remote Similarity	NPD4190	Phase 3
0.5952	Remote Similarity	NPD5275	Approved
0.5918	Remote Similarity	NPD7638	Approved
0.5889	Remote Similarity	NPD3666	Approved
0.5889	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD3133	Approved
0.5889	Remote Similarity	NPD3665	Phase 1
0.5882	Remote Similarity	NPD6920	Discontinued
0.5876	Remote Similarity	NPD5221	Approved
0.5876	Remote Similarity	NPD5222	Approved
0.5876	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD4697	Phase 3
0.5862	Remote Similarity	NPD4195	Approved
0.5862	Remote Similarity	NPD6683	Phase 2
0.5859	Remote Similarity	NPD5285	Approved
0.5859	Remote Similarity	NPD5286	Approved
0.5859	Remote Similarity	NPD4696	Approved
0.5859	Remote Similarity	NPD7639	Approved
0.5859	Remote Similarity	NPD7640	Approved
0.5859	Remote Similarity	NPD4700	Approved
0.5833	Remote Similarity	NPD1810	Approved
0.5833	Remote Similarity	NPD1811	Approved
0.5833	Remote Similarity	NPD7748	Approved
0.5824	Remote Similarity	NPD6893	Approved
0.5818	Remote Similarity	NPD7516	Approved
0.5816	Remote Similarity	NPD5173	Approved
0.5814	Remote Similarity	NPD6925	Approved
0.5814	Remote Similarity	NPD5776	Phase 2
0.58	Remote Similarity	NPD5223	Approved
0.5795	Remote Similarity	NPD7514	Phase 3
0.5747	Remote Similarity	NPD7145	Approved
0.5747	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD4753	Phase 2
0.5743	Remote Similarity	NPD7632	Discontinued
0.5743	Remote Similarity	NPD4633	Approved
0.5743	Remote Similarity	NPD5224	Approved
0.5743	Remote Similarity	NPD5226	Approved
0.5743	Remote Similarity	NPD5211	Phase 2
0.5743	Remote Similarity	NPD5225	Approved
0.5729	Remote Similarity	NPD6399	Phase 3
0.5728	Remote Similarity	NPD6675	Approved
0.5728	Remote Similarity	NPD5739	Approved
0.5728	Remote Similarity	NPD7128	Approved
0.5728	Remote Similarity	NPD6402	Approved
0.5727	Remote Similarity	NPD7328	Approved
0.5727	Remote Similarity	NPD7327	Approved
0.5699	Remote Similarity	NPD7750	Discontinued
0.5686	Remote Similarity	NPD5174	Approved
0.5686	Remote Similarity	NPD5175	Approved
0.5686	Remote Similarity	NPD4754	Approved
0.5667	Remote Similarity	NPD4221	Approved
0.5667	Remote Similarity	NPD4223	Phase 3
0.5663	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.566	Remote Similarity	NPD4634	Approved
0.5657	Remote Similarity	NPD7902	Approved
0.5652	Remote Similarity	NPD5329	Approved
0.5648	Remote Similarity	NPD8133	Approved
0.5636	Remote Similarity	NPD7115	Discovery
0.5631	Remote Similarity	NPD5141	Approved
0.5625	Remote Similarity	NPD8377	Approved
0.5625	Remote Similarity	NPD8294	Approved
0.5619	Remote Similarity	NPD6899	Approved
0.5619	Remote Similarity	NPD6415	Discontinued
0.5619	Remote Similarity	NPD7320	Approved
0.5619	Remote Similarity	NPD6881	Approved
0.5618	Remote Similarity	NPD7332	Phase 2
0.56	Remote Similarity	NPD5290	Discontinued

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