NPASS Compound

Structure

CID111234 OpenBabel06191715462D 30 33 0 0 1 0 0 0 0 0999 V2000 -3.9948 6.3786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5355 5.6921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2021 4.5995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8057 3.7100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -2.4722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5335 2.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7428 3.9130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3464 3.0235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6883 -0.9753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2206 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2203 0.4862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8447 1.4614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6873 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6891 1.9486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8435 0.4877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5669 5.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1706 4.7010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3779 2.9220 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8441 -1.4620 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6885 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3776 1.9481 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9748 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5329 0.4867 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8444 0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5332 1.4609 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 2.5538 -1.4741 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 2 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 11 24 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 25 1 0 0 0 0 14 16 1 0 0 0 0 14 26 1 0 0 0 0 15 17 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 19 1 0 0 0 0 20 4 1 1 0 0 0 20 23 1 0 0 0 0 21 5 1 1 0 0 0 21 24 1 0 0 0 0 21 27 1 0 0 0 0 22 10 1 1 0 0 0 22 25 1 0 0 0 0 22 26 1 0 0 0 0 23 28 1 6 0 0 0 24 29 1 6 0 0 0 25 28 1 6 0 0 0 26 29 1 6 0 0 0 27 30 1 6 0 0 0 28 6 1 6 0 0 0 29 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.39
Volume:	482.068
LogP:	7.867
LogD:	6.729
LogS:	-6.626
# Rotatable Bonds:	5
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.454
Synthetic Accessibility Score:	4.528
Fsp3:	0.931
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:	-4.72
MDCK Permeability:	9.430619684280828e-06
Pgp-inhibitor:	0.976
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.987
30% Bioavailability (F30%):	0.663

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.361
Plasma Protein Binding (PPB):	93.13884735107422%
Volume Distribution (VD):	1.29
Pgp-substrate:	1.7920801639556885%

ADMET: Metabolism

CYP1A2-inhibitor:	0.152
CYP1A2-substrate:	0.57
CYP2C19-inhibitor:	0.096
CYP2C19-substrate:	0.912
CYP2C9-inhibitor:	0.205
CYP2C9-substrate:	0.313
CYP2D6-inhibitor:	0.04
CYP2D6-substrate:	0.748
CYP3A4-inhibitor:	0.399
CYP3A4-substrate:	0.682

ADMET: Excretion

Clearance (CL):	7.121
Half-life (T1/2):	0.035

ADMET: Toxicity

hERG Blockers:	0.968
Human Hepatotoxicity (H-HT):	0.091
Drug-inuced Liver Injury (DILI):	0.878
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.961
Carcinogencity:	0.176
Eye Corrosion:	0.987
Eye Irritation:	0.643
Respiratory Toxicity:	0.38

Download Data

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

Natural Product: NPC111234

Natural Product ID:	NPC111234
*Common Name:**	(3S,4S,5S,8S,9S,10R,13R,14S,17R)-4,10,13-Trimethyl-17-((R)-6-Methyl-5-Methyleneheptan-2-Yl)Hexadecahydro-1H-Cyclopenta[A]Phenanthren-3-Ol
IUPAC Name:	(3S,4S,5S,8S,9S,10R,13R,14S,17R)-4,10,13-trimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms:
Standard InCHIKey:	BTBRBCIRTOKWDH-CNDFOAKRSA-N
Standard InCHI:	InChI=1S/C29H50O/c1-18(2)19(3)8-9-20(4)23-12-13-25-22-10-11-24-21(5)27(30)15-17-29(24,7)26(22)14-16-28(23,25)6/h18,20-27,30H,3,8-17H2,1-2,4-7H3/t20-,21+,22+,23-,24+,25+,26+,27+,28-,29+/m1/s1
SMILES:	CC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4[C@H](C)[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2322192
PubChem CID:	71718619
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO12955	Rumex crispus	Species	Polygonaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1002/ardp.19542870405]
NPO895	Rabdosia inflexa	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/0031-9422(82)80090-3]
NPO268	Bruguiera parviflora	Species	Rhizophoraceae	Eukaryota	n.a.	fruit	n.a.	PMID[15635238]
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20121250]
NPO5183	Feretia apodanthera	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23268742]
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	Hainan soft coral	n.a.	PMID[23357636]
NPO9809	Scutellaria altissima	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO268	Bruguiera parviflora	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12955	Rumex crispus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12955	Rumex crispus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9809	Scutellaria altissima	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO268	Bruguiera parviflora	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12955	Rumex crispus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2158	Guarea kunthiana	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5405	Lycoris incarnata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9809	Scutellaria altissima	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8898	Oplopanax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO895	Rabdosia inflexa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO268	Bruguiera parviflora	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13064	Amietophrynus mauritanicus	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5183	Feretia apodanthera	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11766	Salvia forskahlei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12502	Cordylanthus parviflorus	Species	Orobanchaceae	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
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	=	19500.0	nM	PMID[491461]

☑ 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 NPC111234 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	169
0.1-0.2	2233
0.2-0.3	12398
0.3-0.4	13155
0.4-0.5	5326
0.5-0.6	4806
0.6-0.7	3196
0.7-0.8	1081
0.8-0.85	199
0.85-0.9	77
0.9-0.95	52
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9848	High Similarity	NPC45296
0.9706	High Similarity	NPC192638
0.9706	High Similarity	NPC25511
0.9706	High Similarity	NPC145552
0.9706	High Similarity	NPC196358
0.9706	High Similarity	NPC254509
0.9706	High Similarity	NPC5046
0.9706	High Similarity	NPC62657
0.9706	High Similarity	NPC49168
0.9565	High Similarity	NPC200243
0.9565	High Similarity	NPC185536
0.9565	High Similarity	NPC230704
0.9565	High Similarity	NPC104387
0.9565	High Similarity	NPC240235
0.9565	High Similarity	NPC231256
0.9565	High Similarity	NPC3403
0.9565	High Similarity	NPC70982
0.9565	High Similarity	NPC178383
0.9565	High Similarity	NPC212879
0.9559	High Similarity	NPC195489
0.9429	High Similarity	NPC86305
0.9429	High Similarity	NPC14112
0.9429	High Similarity	NPC93662
0.9429	High Similarity	NPC91573
0.9429	High Similarity	NPC278091
0.9429	High Similarity	NPC78067
0.9429	High Similarity	NPC237460
0.942	High Similarity	NPC308440
0.942	High Similarity	NPC472503
0.9296	High Similarity	NPC257191
0.9296	High Similarity	NPC212241
0.9296	High Similarity	NPC248830
0.9296	High Similarity	NPC331618
0.9296	High Similarity	NPC202540
0.9296	High Similarity	NPC119355
0.9167	High Similarity	NPC477817
0.9167	High Similarity	NPC6978
0.9167	High Similarity	NPC477819
0.9167	High Similarity	NPC31828
0.9167	High Similarity	NPC167037
0.9167	High Similarity	NPC85346
0.9167	High Similarity	NPC138621
0.9167	High Similarity	NPC301707
0.9167	High Similarity	NPC285761
0.9167	High Similarity	NPC472342
0.9167	High Similarity	NPC65897
0.9167	High Similarity	NPC302041
0.9167	High Similarity	NPC102708
0.9167	High Similarity	NPC42853
0.9167	High Similarity	NPC244385
0.9155	High Similarity	NPC189883
0.9091	High Similarity	NPC27243
0.9091	High Similarity	NPC476737
0.9041	High Similarity	NPC80530
0.9041	High Similarity	NPC80297
0.9041	High Similarity	NPC49627
0.9041	High Similarity	NPC273410
0.9041	High Similarity	NPC475727
0.9041	High Similarity	NPC116119
0.9041	High Similarity	NPC49599
0.9041	High Similarity	NPC472742
0.9028	High Similarity	NPC260301
0.9028	High Similarity	NPC307336
0.9028	High Similarity	NPC138502
0.9014	High Similarity	NPC121744
0.9014	High Similarity	NPC118508
0.9014	High Similarity	NPC471723
0.9014	High Similarity	NPC141071
0.9014	High Similarity	NPC322353
0.9014	High Similarity	NPC257347
0.9014	High Similarity	NPC103822
0.8919	High Similarity	NPC102253
0.8919	High Similarity	NPC71535
0.8919	High Similarity	NPC475679
0.8919	High Similarity	NPC13554
0.8919	High Similarity	NPC78545
0.8919	High Similarity	NPC322313
0.8919	High Similarity	NPC236237
0.8904	High Similarity	NPC312328
0.8904	High Similarity	NPC472501
0.8904	High Similarity	NPC472499
0.8904	High Similarity	NPC472500
0.8889	High Similarity	NPC46160
0.8889	High Similarity	NPC38141
0.8889	High Similarity	NPC202642
0.8889	High Similarity	NPC240604
0.8889	High Similarity	NPC129165
0.8889	High Similarity	NPC300324
0.8889	High Similarity	NPC73875
0.8889	High Similarity	NPC134330
0.8873	High Similarity	NPC476736
0.8857	High Similarity	NPC164045
0.8857	High Similarity	NPC301226
0.8784	High Similarity	NPC476316
0.8784	High Similarity	NPC1319
0.8784	High Similarity	NPC24504
0.8767	High Similarity	NPC214570
0.875	High Similarity	NPC162742
0.875	High Similarity	NPC22105
0.875	High Similarity	NPC28657
0.875	High Similarity	NPC230301
0.875	High Similarity	NPC304309
0.875	High Similarity	NPC285893
0.875	High Similarity	NPC134847
0.875	High Similarity	NPC136188
0.875	High Similarity	NPC288035
0.8732	High Similarity	NPC211009
0.8732	High Similarity	NPC201373
0.8732	High Similarity	NPC472506
0.8684	High Similarity	NPC218616
0.8684	High Similarity	NPC477599
0.8684	High Similarity	NPC296701
0.8667	High Similarity	NPC47149
0.8667	High Similarity	NPC236112
0.8667	High Similarity	NPC206735
0.8649	High Similarity	NPC275910
0.8649	High Similarity	NPC475
0.8649	High Similarity	NPC205455
0.8649	High Similarity	NPC472502
0.8649	High Similarity	NPC186191
0.8636	High Similarity	NPC148174
0.8636	High Similarity	NPC218585
0.8636	High Similarity	NPC71460
0.863	High Similarity	NPC321381
0.863	High Similarity	NPC470362
0.863	High Similarity	NPC321016
0.863	High Similarity	NPC107059
0.863	High Similarity	NPC113733
0.8611	High Similarity	NPC469533
0.8611	High Similarity	NPC469593
0.8611	High Similarity	NPC469534
0.8611	High Similarity	NPC100334
0.8571	High Similarity	NPC470929
0.8571	High Similarity	NPC472743
0.8571	High Similarity	NPC113978
0.8571	High Similarity	NPC207013
0.8571	High Similarity	NPC210323
0.8571	High Similarity	NPC85095
0.8571	High Similarity	NPC211135
0.8571	High Similarity	NPC477818
0.8571	High Similarity	NPC232023
0.8571	High Similarity	NPC246956
0.8571	High Similarity	NPC5280
0.8571	High Similarity	NPC216420
0.8571	High Similarity	NPC110778
0.8571	High Similarity	NPC475726
0.8553	High Similarity	NPC474531
0.8553	High Similarity	NPC157655
0.8533	High Similarity	NPC30986
0.8533	High Similarity	NPC472463
0.8533	High Similarity	NPC209430
0.8533	High Similarity	NPC5604
0.8529	High Similarity	NPC473276
0.8529	High Similarity	NPC474380
0.8529	High Similarity	NPC41577
0.8514	High Similarity	NPC155986
0.8514	High Similarity	NPC34019
0.8514	High Similarity	NPC318495
0.8514	High Similarity	NPC198968
0.8507	High Similarity	NPC114891
0.8493	Intermediate Similarity	NPC144075
0.8472	Intermediate Similarity	NPC182717
0.8462	Intermediate Similarity	NPC74595
0.8462	Intermediate Similarity	NPC255882
0.8462	Intermediate Similarity	NPC86238
0.8462	Intermediate Similarity	NPC475745
0.8462	Intermediate Similarity	NPC474482
0.8462	Intermediate Similarity	NPC264665
0.8462	Intermediate Similarity	NPC209802
0.8442	Intermediate Similarity	NPC470049
0.8442	Intermediate Similarity	NPC248886
0.8442	Intermediate Similarity	NPC30166
0.8442	Intermediate Similarity	NPC472504
0.8429	Intermediate Similarity	NPC160209
0.8429	Intermediate Similarity	NPC2648
0.8406	Intermediate Similarity	NPC473929
0.8406	Intermediate Similarity	NPC142712
0.84	Intermediate Similarity	NPC307965
0.84	Intermediate Similarity	NPC474216
0.84	Intermediate Similarity	NPC318136
0.84	Intermediate Similarity	NPC87604
0.84	Intermediate Similarity	NPC477522
0.84	Intermediate Similarity	NPC76931
0.84	Intermediate Similarity	NPC473943
0.84	Intermediate Similarity	NPC18603
0.8382	Intermediate Similarity	NPC219940
0.8382	Intermediate Similarity	NPC68656
0.8382	Intermediate Similarity	NPC101128
0.8382	Intermediate Similarity	NPC69149
0.8382	Intermediate Similarity	NPC144650
0.8378	Intermediate Similarity	NPC244488
0.8378	Intermediate Similarity	NPC30590
0.8378	Intermediate Similarity	NPC290598
0.8378	Intermediate Similarity	NPC122418
0.8378	Intermediate Similarity	NPC265328
0.8378	Intermediate Similarity	NPC120098
0.8378	Intermediate Similarity	NPC247325
0.8378	Intermediate Similarity	NPC27765
0.8354	Intermediate Similarity	NPC264317
0.8354	Intermediate Similarity	NPC294438

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 NPC111234 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	2598
0.2-0.3	4356
0.3-0.4	1422
0.4-0.5	229
0.5-0.6	152
0.6-0.7	154
0.7-0.8	61
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8919	High Similarity	NPD7525	Registered
0.875	High Similarity	NPD6942	Approved
0.875	High Similarity	NPD7339	Approved
0.8354	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD7645	Phase 2
0.7867	Intermediate Similarity	NPD6924	Approved
0.7867	Intermediate Similarity	NPD6926	Approved
0.7838	Intermediate Similarity	NPD7150	Approved
0.7838	Intermediate Similarity	NPD7152	Approved
0.7838	Intermediate Similarity	NPD4243	Approved
0.7838	Intermediate Similarity	NPD7151	Approved
0.7808	Intermediate Similarity	NPD6923	Approved
0.7808	Intermediate Similarity	NPD6922	Approved
0.7778	Intermediate Similarity	NPD4786	Approved
0.7738	Intermediate Similarity	NPD5328	Approved
0.7703	Intermediate Similarity	NPD4787	Phase 1
0.7703	Intermediate Similarity	NPD7144	Approved
0.7703	Intermediate Similarity	NPD7143	Approved
0.7662	Intermediate Similarity	NPD6933	Approved
0.7654	Intermediate Similarity	NPD4788	Approved
0.7632	Intermediate Similarity	NPD4785	Approved
0.7632	Intermediate Similarity	NPD4784	Approved
0.76	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD3618	Phase 1
0.7558	Intermediate Similarity	NPD8035	Phase 2
0.7558	Intermediate Similarity	NPD8034	Phase 2
0.7558	Intermediate Similarity	NPD6079	Approved
0.7531	Intermediate Similarity	NPD3667	Approved
0.75	Intermediate Similarity	NPD4748	Discontinued
0.7436	Intermediate Similarity	NPD6117	Approved
0.7403	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6929	Approved
0.7342	Intermediate Similarity	NPD6116	Phase 1
0.7333	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4190	Phase 3
0.7308	Intermediate Similarity	NPD5275	Approved
0.7294	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6930	Phase 2
0.7284	Intermediate Similarity	NPD6931	Approved
0.7284	Intermediate Similarity	NPD7509	Discontinued
0.7273	Intermediate Similarity	NPD4202	Approved
0.725	Intermediate Similarity	NPD6115	Approved
0.725	Intermediate Similarity	NPD6697	Approved
0.725	Intermediate Similarity	NPD6114	Approved
0.725	Intermediate Similarity	NPD6118	Approved
0.7143	Intermediate Similarity	NPD3666	Approved
0.7143	Intermediate Similarity	NPD3665	Phase 1
0.7143	Intermediate Similarity	NPD3133	Approved
0.7125	Intermediate Similarity	NPD6932	Approved
0.7125	Intermediate Similarity	NPD6925	Approved
0.7125	Intermediate Similarity	NPD5776	Phase 2
0.7089	Intermediate Similarity	NPD3703	Phase 2
0.7065	Intermediate Similarity	NPD7638	Approved
0.7037	Intermediate Similarity	NPD7145	Approved
0.7033	Intermediate Similarity	NPD4697	Phase 3
0.7033	Intermediate Similarity	NPD5221	Approved
0.7033	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5222	Approved
0.7024	Intermediate Similarity	NPD6695	Phase 3
0.7013	Intermediate Similarity	NPD4245	Approved
0.7013	Intermediate Similarity	NPD4244	Approved
0.7013	Intermediate Similarity	NPD4789	Approved
0.6989	Remote Similarity	NPD7639	Approved
0.6989	Remote Similarity	NPD7640	Approved
0.6974	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5360	Phase 3
0.6966	Remote Similarity	NPD7515	Phase 2
0.6957	Remote Similarity	NPD5173	Approved
0.6957	Remote Similarity	NPD4755	Approved
0.6951	Remote Similarity	NPD4195	Approved
0.6951	Remote Similarity	NPD6683	Phase 2
0.6941	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6399	Phase 3
0.6883	Remote Similarity	NPD3698	Phase 2
0.6867	Remote Similarity	NPD6928	Phase 2
0.6867	Remote Similarity	NPD7514	Phase 3
0.686	Remote Similarity	NPD6893	Approved
0.6829	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4700	Approved
0.6809	Remote Similarity	NPD4696	Approved
0.6809	Remote Similarity	NPD5286	Approved
0.6809	Remote Similarity	NPD5285	Approved
0.68	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6902	Approved
0.6782	Remote Similarity	NPD5279	Phase 3
0.6744	Remote Similarity	NPD3668	Phase 3
0.6742	Remote Similarity	NPD4753	Phase 2
0.6737	Remote Similarity	NPD5223	Approved
0.6706	Remote Similarity	NPD4223	Phase 3
0.6706	Remote Similarity	NPD4221	Approved
0.6705	Remote Similarity	NPD7750	Discontinued
0.6705	Remote Similarity	NPD7524	Approved
0.6702	Remote Similarity	NPD5290	Discontinued
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD8264	Approved
0.6667	Remote Similarity	NPD7332	Phase 2
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD5224	Approved
0.6633	Remote Similarity	NPD6402	Approved
0.6633	Remote Similarity	NPD7128	Approved
0.6633	Remote Similarity	NPD5739	Approved
0.6633	Remote Similarity	NPD6675	Approved
0.663	Remote Similarity	NPD7748	Approved
0.6627	Remote Similarity	NPD3671	Phase 1
0.6598	Remote Similarity	NPD4754	Approved
0.6598	Remote Similarity	NPD5174	Approved
0.6598	Remote Similarity	NPD5175	Approved
0.6588	Remote Similarity	NPD6898	Phase 1
0.6552	Remote Similarity	NPD4197	Approved
0.6538	Remote Similarity	NPD6705	Phase 1
0.6531	Remote Similarity	NPD5141	Approved
0.6515	Remote Similarity	NPD384	Approved
0.6515	Remote Similarity	NPD385	Approved
0.65	Remote Similarity	NPD4758	Discontinued
0.65	Remote Similarity	NPD6881	Approved
0.65	Remote Similarity	NPD6899	Approved
0.65	Remote Similarity	NPD7320	Approved
0.6495	Remote Similarity	NPD7632	Discontinued
0.6465	Remote Similarity	NPD4768	Approved
0.6465	Remote Similarity	NPD4767	Approved
0.6444	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD6373	Approved
0.6436	Remote Similarity	NPD6372	Approved
0.6429	Remote Similarity	NPD3617	Approved
0.6421	Remote Similarity	NPD7902	Approved
0.6421	Remote Similarity	NPD6083	Phase 2
0.6421	Remote Similarity	NPD6084	Phase 2
0.6413	Remote Similarity	NPD7087	Discontinued
0.6404	Remote Similarity	NPD4138	Approved
0.6404	Remote Similarity	NPD4690	Approved
0.6404	Remote Similarity	NPD4689	Approved
0.6404	Remote Similarity	NPD7334	Approved
0.6404	Remote Similarity	NPD6409	Approved
0.6404	Remote Similarity	NPD4693	Phase 3
0.6404	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5330	Approved
0.6404	Remote Similarity	NPD6684	Approved
0.6404	Remote Similarity	NPD7146	Approved
0.6404	Remote Similarity	NPD7521	Approved
0.6404	Remote Similarity	NPD5205	Approved
0.6404	Remote Similarity	NPD4688	Approved
0.64	Remote Similarity	NPD5697	Approved
0.64	Remote Similarity	NPD5701	Approved
0.6383	Remote Similarity	NPD4629	Approved
0.6383	Remote Similarity	NPD5210	Approved
0.6374	Remote Similarity	NPD6051	Approved
0.6373	Remote Similarity	NPD7102	Approved
0.6373	Remote Similarity	NPD7290	Approved
0.6373	Remote Similarity	NPD6883	Approved
0.6337	Remote Similarity	NPD5128	Approved
0.6337	Remote Similarity	NPD6011	Approved
0.6337	Remote Similarity	NPD4730	Approved
0.6337	Remote Similarity	NPD5168	Approved
0.6337	Remote Similarity	NPD4729	Approved
0.6311	Remote Similarity	NPD6617	Approved
0.6311	Remote Similarity	NPD8130	Phase 1
0.6311	Remote Similarity	NPD6847	Approved
0.6311	Remote Similarity	NPD6649	Approved
0.6311	Remote Similarity	NPD6869	Approved
0.6311	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6650	Approved
0.6304	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6700	Approved
0.6296	Remote Similarity	NPD6081	Approved
0.6282	Remote Similarity	NPD4224	Phase 2
0.6275	Remote Similarity	NPD6014	Approved
0.6275	Remote Similarity	NPD6012	Approved
0.6275	Remote Similarity	NPD6013	Approved
0.6264	Remote Similarity	NPD6672	Approved
0.6264	Remote Similarity	NPD6903	Approved
0.6264	Remote Similarity	NPD5737	Approved
0.6264	Remote Similarity	NPD4722	Approved
0.6264	Remote Similarity	NPD4723	Approved
0.625	Remote Similarity	NPD6882	Approved
0.625	Remote Similarity	NPD8297	Approved
0.6237	Remote Similarity	NPD6702	Approved
0.6237	Remote Similarity	NPD6703	Approved
0.6235	Remote Similarity	NPD5364	Discontinued
0.6224	Remote Similarity	NPD4159	Approved
0.6222	Remote Similarity	NPD4694	Approved
0.6222	Remote Similarity	NPD5690	Phase 2
0.6222	Remote Similarity	NPD5280	Approved
0.6214	Remote Similarity	NPD5248	Approved
0.6214	Remote Similarity	NPD5135	Approved
0.6214	Remote Similarity	NPD5250	Approved
0.6214	Remote Similarity	NPD5247	Approved
0.6214	Remote Similarity	NPD5249	Phase 3
0.6214	Remote Similarity	NPD5251	Approved
0.6214	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4634	Approved
0.6214	Remote Similarity	NPD5169	Approved
0.6207	Remote Similarity	NPD4139	Approved
0.6207	Remote Similarity	NPD4692	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