NPASS Compound

Structure

CID207013 OpenBabel06191715592D 34 37 0 0 1 0 0 0 0 0999 V2000 4.6110 0.7284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1898 -0.0921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2849 -2.8795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1358 -2.3883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4640 0.5087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8809 -1.4570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0009 2.8431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2425 1.5489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1899 1.5488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6416 0.9478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6427 -1.8967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7688 2.3693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6415 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8214 -1.4225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6427 0.9478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2848 0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6636 0.7284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8214 1.4220 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8213 1.4220 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1056 -0.4741 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4641 -1.4225 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6427 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9478 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1056 -1.4225 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2848 -1.8967 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4640 -0.4741 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8214 -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 1 0 0 0 0 0 0 0 0 0 0.8214 2.3694 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8213 2.3954 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9487 0.0125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9487 -1.9091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8214 3.3168 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 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 9 10 1 0 0 0 0 9 13 1 0 0 0 0 10 18 2 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 15 1 0 0 0 0 12 22 1 0 0 0 0 13 30 1 0 0 0 0 14 29 1 0 0 0 0 15 28 1 0 0 0 0 16 20 1 0 0 0 0 16 23 1 0 0 0 0 17 21 1 0 0 0 0 17 27 1 0 0 0 0 19 24 1 0 0 0 0 19 30 1 1 0 0 0 20 24 1 0 0 0 0 20 31 1 1 0 0 0 21 25 1 0 0 0 0 21 32 1 6 0 0 0 22 26 1 0 0 0 0 22 27 1 1 0 0 0 23 27 1 1 0 0 0 23 28 1 0 0 0 0 24 29 1 6 0 0 0 25 26 1 0 0 0 0 25 33 1 1 0 0 0 27 5 1 1 0 0 0 28 29 1 6 0 0 0 29 7 1 6 0 0 0 30 8 1 6 0 0 0 30 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.39
Volume:	525.735
LogP:	5.22
LogD:	4.69
LogS:	-4.609
# Rotatable Bonds:	4
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.406
Synthetic Accessibility Score:	5.023
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.833
MDCK Permeability:	2.4628772735013627e-05
Pgp-inhibitor:	0.949
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.213
30% Bioavailability (F30%):	0.785

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	93.83696746826172%
Volume Distribution (VD):	0.95
Pgp-substrate:	3.326323986053467%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.154
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.889
CYP2C9-inhibitor:	0.159
CYP2C9-substrate:	0.795
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.237
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	2.901
Half-life (T1/2):	0.205

ADMET: Toxicity

hERG Blockers:	0.093
Human Hepatotoxicity (H-HT):	0.382
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.09
Maximum Recommended Daily Dose:	0.074
Skin Sensitization:	0.644
Carcinogencity:	0.004
Eye Corrosion:	0.072
Eye Irritation:	0.424
Respiratory Toxicity:	0.919

Download Data

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

Natural Product: NPC207013

Natural Product ID:	NPC207013
*Common Name:**	20S-Dammar-24-En-2Alpha,3Beta,12Beta,20-Tetrol
IUPAC Name:	(2R,3R,5R,8R,9R,10R,12R,13R,14R,17S)-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-2,3,12-triol
Synonyms:
Standard InCHIKey:	HEPDUIXFAHPBLL-GNTCEATOSA-N
Standard InCHI:	InChI=1S/C30H52O4/c1-18(2)10-9-13-30(8,34)19-11-14-29(7)24(19)20(31)16-23-27(5)17-21(32)25(33)26(3,4)22(27)12-15-28(23,29)6/h10,19-25,31-34H,9,11-17H2,1-8H3/t19-,20+,21+,22-,23+,24-,25-,27-,28+,29+,30-/m0/s1
SMILES:	CC(=CCC[C@@]([C@H]1CC[C@@]2([C@@H]1[C@H](O)C[C@H]1[C@@]2(C)CC[C@@H]2[C@]1(C)C[C@@H](O)[C@@H](C2(C)C)O)C)(O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3099607
PubChem CID:	13387879
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	Stems	n.a.	n.a.	PMID[20104880]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22342101]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[25895106]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16506	Synotis alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4305	Pertusaria wulfenii	Species	Pertusariaceae	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
EC50	1
IC50	1
Others	2

Activity Type	# Activity
Cell Line	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	12.54	ug.mL-1	PMID[539161]
NPT2	Others	Unspecified		EC50	=	5100.0	nM	PMID[539162]
NPT2	Others	Unspecified		FC	=	2.4	n.a.	PMID[539162]
NPT2	Others	Unspecified		Inhibition	=	25.0	%	PMID[539162]

☑ 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 NPC207013 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	176
0.1-0.2	1474
0.2-0.3	6304
0.3-0.4	15614
0.4-0.5	7593
0.5-0.6	4753
0.6-0.7	4611
0.7-0.8	1796
0.8-0.85	289
0.85-0.9	58
0.9-0.95	22
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.961	High Similarity	NPC236237
0.961	High Similarity	NPC13554
0.961	High Similarity	NPC102253
0.961	High Similarity	NPC322313
0.9481	High Similarity	NPC80530
0.9481	High Similarity	NPC273410
0.9367	High Similarity	NPC30166
0.9359	High Similarity	NPC236112
0.9351	High Similarity	NPC244385
0.9351	High Similarity	NPC138621
0.9351	High Similarity	NPC6978
0.9351	High Similarity	NPC167037
0.9351	High Similarity	NPC285761
0.9241	High Similarity	NPC474531
0.9091	High Similarity	NPC91573
0.9091	High Similarity	NPC237460
0.9048	High Similarity	NPC105495
0.9048	High Similarity	NPC109744
0.9036	High Similarity	NPC186145
0.9036	High Similarity	NPC470620
0.9036	High Similarity	NPC474657
0.9012	High Similarity	NPC211135
0.9012	High Similarity	NPC85095
0.9012	High Similarity	NPC110778
0.9012	High Similarity	NPC216420
0.8987	High Similarity	NPC328714
0.8961	High Similarity	NPC3403
0.8941	High Similarity	NPC475751
0.8941	High Similarity	NPC473956
0.8929	High Similarity	NPC67872
0.8929	High Similarity	NPC133588
0.8929	High Similarity	NPC474668
0.8929	High Similarity	NPC475664
0.8916	High Similarity	NPC71520
0.8916	High Similarity	NPC201273
0.8916	High Similarity	NPC94462
0.8916	High Similarity	NPC269058
0.8889	High Similarity	NPC218616
0.8889	High Similarity	NPC296701
0.8875	High Similarity	NPC22403
0.8861	High Similarity	NPC301707
0.8861	High Similarity	NPC102708
0.8861	High Similarity	NPC85346
0.8861	High Similarity	NPC302041
0.8861	High Similarity	NPC65897
0.8846	High Similarity	NPC189883
0.878	High Similarity	NPC474634
0.878	High Similarity	NPC141941
0.878	High Similarity	NPC253402
0.878	High Similarity	NPC477818
0.878	High Similarity	NPC317458
0.878	High Similarity	NPC159168
0.878	High Similarity	NPC193870
0.8765	High Similarity	NPC6707
0.8765	High Similarity	NPC70927
0.875	High Similarity	NPC1319
0.8734	High Similarity	NPC155986
0.8734	High Similarity	NPC318495
0.8734	High Similarity	NPC198968
0.8734	High Similarity	NPC214570
0.8718	High Similarity	NPC471723
0.8718	High Similarity	NPC141071
0.8718	High Similarity	NPC257347
0.869	High Similarity	NPC24277
0.869	High Similarity	NPC6605
0.869	High Similarity	NPC477604
0.869	High Similarity	NPC121981
0.869	High Similarity	NPC125399
0.8675	High Similarity	NPC185568
0.8675	High Similarity	NPC478102
0.8675	High Similarity	NPC475798
0.8675	High Similarity	NPC127606
0.8675	High Similarity	NPC255882
0.8675	High Similarity	NPC124172
0.8675	High Similarity	NPC238992
0.8659	High Similarity	NPC7988
0.8659	High Similarity	NPC477599
0.8659	High Similarity	NPC47763
0.8625	High Similarity	NPC312328
0.8625	High Similarity	NPC275910
0.8621	High Similarity	NPC41554
0.8621	High Similarity	NPC275671
0.8621	High Similarity	NPC97404
0.8621	High Similarity	NPC210268
0.8608	High Similarity	NPC73875
0.8608	High Similarity	NPC321381
0.8608	High Similarity	NPC240604
0.8608	High Similarity	NPC477925
0.8608	High Similarity	NPC274079
0.8608	High Similarity	NPC134330
0.8608	High Similarity	NPC107059
0.8608	High Similarity	NPC129165
0.8608	High Similarity	NPC202642
0.8608	High Similarity	NPC14112
0.8608	High Similarity	NPC46160
0.8608	High Similarity	NPC321016
0.8608	High Similarity	NPC86305
0.8608	High Similarity	NPC300324
0.8605	High Similarity	NPC470361
0.8571	High Similarity	NPC318390
0.8571	High Similarity	NPC111234
0.8571	High Similarity	NPC167706
0.8554	High Similarity	NPC470558
0.8554	High Similarity	NPC82623
0.8554	High Similarity	NPC134481
0.8554	High Similarity	NPC113978
0.8519	High Similarity	NPC472463
0.8519	High Similarity	NPC30986
0.8519	High Similarity	NPC209430
0.8506	High Similarity	NPC3345
0.8506	High Similarity	NPC291484
0.8506	High Similarity	NPC204188
0.8506	High Similarity	NPC11216
0.8506	High Similarity	NPC329596
0.8506	High Similarity	NPC80561
0.85	High Similarity	NPC470758
0.85	High Similarity	NPC130136
0.85	High Similarity	NPC477924
0.85	High Similarity	NPC470711
0.8488	Intermediate Similarity	NPC280556
0.8481	Intermediate Similarity	NPC162742
0.8481	Intermediate Similarity	NPC104387
0.8481	Intermediate Similarity	NPC240235
0.8481	Intermediate Similarity	NPC322353
0.8481	Intermediate Similarity	NPC477923
0.8481	Intermediate Similarity	NPC22105
0.8481	Intermediate Similarity	NPC230301
0.8481	Intermediate Similarity	NPC178383
0.8481	Intermediate Similarity	NPC136188
0.8481	Intermediate Similarity	NPC66566
0.8481	Intermediate Similarity	NPC304309
0.8481	Intermediate Similarity	NPC285893
0.8481	Intermediate Similarity	NPC118508
0.8481	Intermediate Similarity	NPC28657
0.8481	Intermediate Similarity	NPC185536
0.8481	Intermediate Similarity	NPC70982
0.8481	Intermediate Similarity	NPC230704
0.8481	Intermediate Similarity	NPC121744
0.8481	Intermediate Similarity	NPC288035
0.8481	Intermediate Similarity	NPC134847
0.8481	Intermediate Similarity	NPC212879
0.8481	Intermediate Similarity	NPC231256
0.8471	Intermediate Similarity	NPC237344
0.8471	Intermediate Similarity	NPC139724
0.8471	Intermediate Similarity	NPC6391
0.8471	Intermediate Similarity	NPC261266
0.8462	Intermediate Similarity	NPC474140
0.8452	Intermediate Similarity	NPC209802
0.8452	Intermediate Similarity	NPC205845
0.8452	Intermediate Similarity	NPC474493
0.8452	Intermediate Similarity	NPC470077
0.8444	Intermediate Similarity	NPC471903
0.8442	Intermediate Similarity	NPC45296
0.8434	Intermediate Similarity	NPC470049
0.8434	Intermediate Similarity	NPC470614
0.8434	Intermediate Similarity	NPC1272
0.8434	Intermediate Similarity	NPC101462
0.8434	Intermediate Similarity	NPC49964
0.8434	Intermediate Similarity	NPC248886
0.8434	Intermediate Similarity	NPC87489
0.8415	Intermediate Similarity	NPC287749
0.8415	Intermediate Similarity	NPC71535
0.8415	Intermediate Similarity	NPC241290
0.8415	Intermediate Similarity	NPC164840
0.8415	Intermediate Similarity	NPC78545
0.8415	Intermediate Similarity	NPC209944
0.8409	Intermediate Similarity	NPC189520
0.8395	Intermediate Similarity	NPC473943
0.8395	Intermediate Similarity	NPC477819
0.8395	Intermediate Similarity	NPC186191
0.8395	Intermediate Similarity	NPC472342
0.8395	Intermediate Similarity	NPC477522
0.8395	Intermediate Similarity	NPC474216
0.8395	Intermediate Similarity	NPC31828
0.8395	Intermediate Similarity	NPC87604
0.8395	Intermediate Similarity	NPC205455
0.8395	Intermediate Similarity	NPC300499
0.8395	Intermediate Similarity	NPC42853
0.8395	Intermediate Similarity	NPC477817
0.8391	Intermediate Similarity	NPC477606
0.8391	Intermediate Similarity	NPC32830
0.8375	Intermediate Similarity	NPC78067
0.8375	Intermediate Similarity	NPC113733
0.8375	Intermediate Similarity	NPC278091
0.8375	Intermediate Similarity	NPC470362
0.8375	Intermediate Similarity	NPC470749
0.8375	Intermediate Similarity	NPC315261
0.8375	Intermediate Similarity	NPC93662
0.8372	Intermediate Similarity	NPC477600
0.8354	Intermediate Similarity	NPC100334
0.8354	Intermediate Similarity	NPC25511
0.8354	Intermediate Similarity	NPC196358
0.8354	Intermediate Similarity	NPC145552
0.8354	Intermediate Similarity	NPC62657
0.8354	Intermediate Similarity	NPC308440
0.8354	Intermediate Similarity	NPC192638
0.8354	Intermediate Similarity	NPC472503
0.8354	Intermediate Similarity	NPC5046
0.8354	Intermediate Similarity	NPC49168
0.8354	Intermediate Similarity	NPC254509

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 NPC207013 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	1693
0.2-0.3	4422
0.3-0.4	2044
0.4-0.5	410
0.5-0.6	150
0.6-0.7	182
0.7-0.8	88
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.961	High Similarity	NPD7525	Registered
0.8481	Intermediate Similarity	NPD7339	Approved
0.8481	Intermediate Similarity	NPD6942	Approved
0.8375	Intermediate Similarity	NPD6933	Approved
0.8148	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6926	Approved
0.8125	Intermediate Similarity	NPD6924	Approved
0.8077	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD7645	Phase 2
0.7875	Intermediate Similarity	NPD4243	Approved
0.7816	Intermediate Similarity	NPD4786	Approved
0.7778	Intermediate Similarity	NPD5328	Approved
0.7765	Intermediate Similarity	NPD7509	Discontinued
0.7753	Intermediate Similarity	NPD7524	Approved
0.7717	Intermediate Similarity	NPD4202	Approved
0.7683	Intermediate Similarity	NPD4784	Approved
0.7683	Intermediate Similarity	NPD4785	Approved
0.7654	Intermediate Similarity	NPD7150	Approved
0.7654	Intermediate Similarity	NPD7152	Approved
0.7654	Intermediate Similarity	NPD7151	Approved
0.764	Intermediate Similarity	NPD3618	Phase 1
0.7625	Intermediate Similarity	NPD6923	Approved
0.7625	Intermediate Similarity	NPD6922	Approved
0.7614	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6079	Approved
0.7586	Intermediate Similarity	NPD3667	Approved
0.7579	Intermediate Similarity	NPD4755	Approved
0.7558	Intermediate Similarity	NPD6930	Phase 2
0.7558	Intermediate Similarity	NPD4748	Discontinued
0.7558	Intermediate Similarity	NPD6931	Approved
0.7556	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD7143	Approved
0.7531	Intermediate Similarity	NPD7144	Approved
0.7528	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6695	Phase 3
0.7442	Intermediate Similarity	NPD6929	Approved
0.7423	Intermediate Similarity	NPD4700	Approved
0.7423	Intermediate Similarity	NPD4696	Approved
0.7423	Intermediate Similarity	NPD5285	Approved
0.7423	Intermediate Similarity	NPD5286	Approved
0.7412	Intermediate Similarity	NPD6932	Approved
0.7381	Intermediate Similarity	NPD5275	Approved
0.7381	Intermediate Similarity	NPD4190	Phase 3
0.7347	Intermediate Similarity	NPD5223	Approved
0.734	Intermediate Similarity	NPD6399	Phase 3
0.732	Intermediate Similarity	NPD7638	Approved
0.7292	Intermediate Similarity	NPD5222	Approved
0.7292	Intermediate Similarity	NPD5221	Approved
0.7292	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4697	Phase 3
0.7273	Intermediate Similarity	NPD4633	Approved
0.7273	Intermediate Similarity	NPD5225	Approved
0.7273	Intermediate Similarity	NPD5226	Approved
0.7273	Intermediate Similarity	NPD5224	Approved
0.7273	Intermediate Similarity	NPD5211	Phase 2
0.7245	Intermediate Similarity	NPD7640	Approved
0.7245	Intermediate Similarity	NPD7639	Approved
0.7241	Intermediate Similarity	NPD4195	Approved
0.7241	Intermediate Similarity	NPD6683	Phase 2
0.7234	Intermediate Similarity	NPD7515	Phase 2
0.7234	Intermediate Similarity	NPD8035	Phase 2
0.7234	Intermediate Similarity	NPD8034	Phase 2
0.7228	Intermediate Similarity	NPD6402	Approved
0.7228	Intermediate Similarity	NPD7128	Approved
0.7228	Intermediate Similarity	NPD6675	Approved
0.7228	Intermediate Similarity	NPD5739	Approved
0.7222	Intermediate Similarity	NPD3133	Approved
0.7222	Intermediate Similarity	NPD3665	Phase 1
0.7222	Intermediate Similarity	NPD3666	Approved
0.7216	Intermediate Similarity	NPD5173	Approved
0.7209	Intermediate Similarity	NPD6925	Approved
0.7209	Intermediate Similarity	NPD5776	Phase 2
0.7204	Intermediate Similarity	NPD4753	Phase 2
0.72	Intermediate Similarity	NPD5175	Approved
0.72	Intermediate Similarity	NPD5174	Approved
0.72	Intermediate Similarity	NPD4754	Approved
0.7174	Intermediate Similarity	NPD7750	Discontinued
0.7159	Intermediate Similarity	NPD7514	Phase 3
0.7143	Intermediate Similarity	NPD6893	Approved
0.7129	Intermediate Similarity	NPD5141	Approved
0.7126	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7145	Approved
0.7115	Intermediate Similarity	NPD4634	Approved
0.7111	Intermediate Similarity	NPD4788	Approved
0.7108	Intermediate Similarity	NPD4787	Phase 1
0.7087	Intermediate Similarity	NPD6899	Approved
0.7087	Intermediate Similarity	NPD7320	Approved
0.7087	Intermediate Similarity	NPD6881	Approved
0.7064	Intermediate Similarity	NPD7516	Approved
0.7059	Intermediate Similarity	NPD4768	Approved
0.7059	Intermediate Similarity	NPD4767	Approved
0.7033	Intermediate Similarity	NPD3668	Phase 3
0.7019	Intermediate Similarity	NPD6373	Approved
0.7019	Intermediate Similarity	NPD6372	Approved
0.7011	Intermediate Similarity	NPD6116	Phase 1
0.7	Intermediate Similarity	NPD4221	Approved
0.7	Intermediate Similarity	NPD4223	Phase 3
0.699	Remote Similarity	NPD5701	Approved
0.699	Remote Similarity	NPD5697	Approved
0.6981	Remote Similarity	NPD8297	Approved
0.6972	Remote Similarity	NPD7328	Approved
0.6972	Remote Similarity	NPD7327	Approved
0.6966	Remote Similarity	NPD7332	Phase 2
0.6957	Remote Similarity	NPD5329	Approved
0.6952	Remote Similarity	NPD7290	Approved
0.6952	Remote Similarity	NPD6883	Approved
0.6952	Remote Similarity	NPD7102	Approved
0.6923	Remote Similarity	NPD4729	Approved
0.6923	Remote Similarity	NPD6011	Approved
0.6923	Remote Similarity	NPD4730	Approved
0.6923	Remote Similarity	NPD5128	Approved
0.6916	Remote Similarity	NPD4632	Approved
0.6907	Remote Similarity	NPD7748	Approved
0.6897	Remote Similarity	NPD6117	Approved
0.6889	Remote Similarity	NPD6898	Phase 1
0.6889	Remote Similarity	NPD6902	Approved
0.6887	Remote Similarity	NPD6869	Approved
0.6887	Remote Similarity	NPD8130	Phase 1
0.6887	Remote Similarity	NPD6649	Approved
0.6887	Remote Similarity	NPD6650	Approved
0.6887	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6847	Approved
0.6887	Remote Similarity	NPD6617	Approved
0.6882	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5279	Phase 3
0.6875	Remote Similarity	NPD7087	Discontinued
0.6869	Remote Similarity	NPD7902	Approved
0.6869	Remote Similarity	NPD6083	Phase 2
0.6869	Remote Similarity	NPD6084	Phase 2
0.6857	Remote Similarity	NPD6013	Approved
0.6857	Remote Similarity	NPD6014	Approved
0.6857	Remote Similarity	NPD6012	Approved
0.6848	Remote Similarity	NPD4197	Approved
0.6847	Remote Similarity	NPD8294	Approved
0.6847	Remote Similarity	NPD8377	Approved
0.6842	Remote Similarity	NPD6051	Approved
0.6837	Remote Similarity	NPD4629	Approved
0.6837	Remote Similarity	NPD5210	Approved
0.6832	Remote Similarity	NPD4159	Approved
0.6824	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6882	Approved
0.68	Remote Similarity	NPD5290	Discontinued
0.6792	Remote Similarity	NPD5250	Approved
0.6792	Remote Similarity	NPD5135	Approved
0.6792	Remote Similarity	NPD5249	Phase 3
0.6792	Remote Similarity	NPD5251	Approved
0.6792	Remote Similarity	NPD5169	Approved
0.6792	Remote Similarity	NPD5248	Approved
0.6792	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5247	Approved
0.6786	Remote Similarity	NPD8296	Approved
0.6786	Remote Similarity	NPD8380	Approved
0.6786	Remote Similarity	NPD8379	Approved
0.6786	Remote Similarity	NPD8378	Approved
0.6786	Remote Similarity	NPD8335	Approved
0.6786	Remote Similarity	NPD8033	Approved
0.6782	Remote Similarity	NPD8264	Approved
0.6742	Remote Similarity	NPD6697	Approved
0.6742	Remote Similarity	NPD6118	Approved
0.6742	Remote Similarity	NPD6114	Approved
0.6742	Remote Similarity	NPD6115	Approved
0.6729	Remote Similarity	NPD5215	Approved
0.6729	Remote Similarity	NPD5127	Approved
0.6729	Remote Similarity	NPD5217	Approved
0.6729	Remote Similarity	NPD5216	Approved
0.6727	Remote Similarity	NPD7115	Discovery
0.6702	Remote Similarity	NPD4693	Phase 3
0.6702	Remote Similarity	NPD4688	Approved
0.6702	Remote Similarity	NPD4690	Approved
0.6702	Remote Similarity	NPD4689	Approved
0.6702	Remote Similarity	NPD5205	Approved
0.6702	Remote Similarity	NPD4138	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD4225	Approved
0.6604	Remote Similarity	NPD5168	Approved
0.6602	Remote Similarity	NPD7632	Discontinued
0.6588	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6009	Approved
0.6566	Remote Similarity	NPD7900	Approved
0.6566	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4723	Approved
0.6562	Remote Similarity	NPD4722	Approved
0.6562	Remote Similarity	NPD6672	Approved
0.6562	Remote Similarity	NPD5737	Approved
0.6562	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7507	Approved
0.6549	Remote Similarity	NPD6054	Approved
0.6549	Remote Similarity	NPD6059	Approved
0.6549	Remote Similarity	NPD6319	Approved
0.6545	Remote Similarity	NPD5167	Approved
0.6543	Remote Similarity	NPD368	Approved
0.6531	Remote Similarity	NPD5284	Approved
0.6531	Remote Similarity	NPD5281	Approved
0.6526	Remote Similarity	NPD7521	Approved
0.6526	Remote Similarity	NPD5330	Approved
0.6526	Remote Similarity	NPD6684	Approved
0.6526	Remote Similarity	NPD7146	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