NPASS Compound

Structure

NPC167037 OpenBabel07101719252D 33 36 0 0 1 0 0 0 0 0999 V2000 -4.9735 -0.7186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2259 -1.8462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4176 -3.4085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0143 2.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0414 2.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4469 0.4024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6714 -2.1647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6231 -2.3670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0203 -2.8878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3399 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7680 -0.1858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2742 -1.6439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0686 -2.6855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7680 -1.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.9459 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8426 1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8426 -0.4865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3705 0.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8426 -1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6852 0.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5279 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8426 -0.4865 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 -0.0000 -2.9189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 2.4324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2131 1.4595 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 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 18 2 0 0 0 0 11 19 2 0 0 0 0 12 15 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 21 1 0 0 0 0 16 23 1 0 0 0 0 17 22 1 0 0 0 0 17 30 1 0 0 0 0 20 19 1 1 0 0 0 20 25 1 0 0 0 0 21 25 1 0 0 0 0 21 31 1 1 0 0 0 22 26 1 0 0 0 0 22 32 1 6 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 24 33 1 1 0 0 0 25 29 1 6 0 0 0 26 27 1 0 0 0 0 26 28 1 1 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:	458.38
Volume:	514.308
LogP:	5.891
LogD:	5.241
LogS:	-5.017
# Rotatable Bonds:	3
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.436
Synthetic Accessibility Score:	5.053
Fsp3:	0.867
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:	-4.849
MDCK Permeability:	4.09363565267995e-05
Pgp-inhibitor:	0.812
Pgp-substrate:	0.795
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.943

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	98.57616424560547%
Volume Distribution (VD):	1.447
Pgp-substrate:	3.82037615776062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.302
CYP2C19-inhibitor:	0.08
CYP2C19-substrate:	0.874
CYP2C9-inhibitor:	0.271
CYP2C9-substrate:	0.66
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.377
CYP3A4-inhibitor:	0.663
CYP3A4-substrate:	0.39

ADMET: Excretion

Clearance (CL):	6.542
Half-life (T1/2):	0.212

ADMET: Toxicity

hERG Blockers:	0.089
Human Hepatotoxicity (H-HT):	0.681
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.623
Maximum Recommended Daily Dose:	0.773
Skin Sensitization:	0.715
Carcinogencity:	0.014
Eye Corrosion:	0.048
Eye Irritation:	0.067
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: NPC167037

Natural Product ID:	NPC167037
*Common Name:**	Damara-20(22), 24-Dien-3, 6, 12-Trine
IUPAC Name:	(3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-4,4,8,10,14-pentamethyl-17-[(2Z)-6-methylhepta-2,5-dien-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,6,12-triol
Synonyms:
Standard InCHIKey:	JKPOYAJYRYOGBN-SQORPJEFSA-N
Standard InCHI:	InChI=1S/C30H50O3/c1-18(2)10-9-11-19(3)20-12-15-29(7)25(20)21(31)16-23-28(6)14-13-24(33)27(4,5)26(28)22(32)17-30(23,29)8/h10-11,20-26,31-33H,9,12-17H2,1-8H3/b19-11-/t20-,21-,22+,23-,24+,25+,26+,28-,29-,30-/m1/s1
SMILES:	CC(=CC/C=C([C@H]1CC[C@@]2([C@@H]1[C@H](O)C[C@H]1[C@@]2(C)C[C@@H]([C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)O)C)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1096728
PubChem CID:	46887682
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
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	leaves and stems	n.a.	n.a.	PMID[25442304]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20712	Panax quinquefolius	Species	Araliaceae	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	2
Others	2

Activity Type	# Activity
Cell Line	2
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1044	Individual Protein	DNA topoisomerase II alpha	Homo sapiens	IC50	>	250000.0	nM	PMID[470267]
NPT143	Individual Protein	DNA topoisomerase I	Homo sapiens	IC50	>	250000.0	nM	PMID[470267]
NPT380	Cell Line	U-251	Homo sapiens	Activity	=	92.68	%	PMID[470268]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	75.59	%	PMID[470268]

☑ 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 NPC167037 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	157
0.1-0.2	1416
0.2-0.3	7107
0.3-0.4	15968
0.4-0.5	6861
0.5-0.6	4873
0.6-0.7	4144
0.7-0.8	1695
0.8-0.85	273
0.85-0.9	157
0.9-0.95	34
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC244385
1.0	High Similarity	NPC138621
1.0	High Similarity	NPC6978
0.9863	High Similarity	NPC273410
0.9863	High Similarity	NPC80530
0.973	High Similarity	NPC102253
0.973	High Similarity	NPC322313
0.973	High Similarity	NPC236237
0.9726	High Similarity	NPC285761
0.9722	High Similarity	NPC237460
0.9467	High Similarity	NPC13554
0.9459	High Similarity	NPC85346
0.9459	High Similarity	NPC65897
0.9459	High Similarity	NPC302041
0.9452	High Similarity	NPC189883
0.9351	High Similarity	NPC477818
0.9351	High Similarity	NPC207013
0.9351	High Similarity	NPC110778
0.9333	High Similarity	NPC1319
0.9324	High Similarity	NPC214570
0.9315	High Similarity	NPC257347
0.9315	High Similarity	NPC141071
0.9315	High Similarity	NPC3403
0.9315	High Similarity	NPC471723
0.9221	High Similarity	NPC218616
0.9221	High Similarity	NPC296701
0.9211	High Similarity	NPC236112
0.92	High Similarity	NPC312328
0.92	High Similarity	NPC275910
0.9189	High Similarity	NPC129165
0.9189	High Similarity	NPC202642
0.9189	High Similarity	NPC14112
0.9189	High Similarity	NPC46160
0.9189	High Similarity	NPC321016
0.9189	High Similarity	NPC86305
0.9189	High Similarity	NPC321381
0.9189	High Similarity	NPC240604
0.9189	High Similarity	NPC134330
0.9189	High Similarity	NPC73875
0.9189	High Similarity	NPC300324
0.9189	High Similarity	NPC107059
0.9167	High Similarity	NPC111234
0.9103	High Similarity	NPC113978
0.9103	High Similarity	NPC193870
0.9103	High Similarity	NPC141941
0.9091	High Similarity	NPC474531
0.9079	High Similarity	NPC472463
0.9079	High Similarity	NPC30986
0.9079	High Similarity	NPC209430
0.9067	High Similarity	NPC318495
0.9067	High Similarity	NPC155986
0.9067	High Similarity	NPC198968
0.9054	High Similarity	NPC136188
0.9054	High Similarity	NPC134847
0.9054	High Similarity	NPC231256
0.9054	High Similarity	NPC70982
0.9054	High Similarity	NPC118508
0.9054	High Similarity	NPC28657
0.9054	High Similarity	NPC322353
0.9054	High Similarity	NPC22105
0.9054	High Similarity	NPC230301
0.9054	High Similarity	NPC121744
0.9054	High Similarity	NPC304309
0.9054	High Similarity	NPC240235
0.9054	High Similarity	NPC285893
0.9054	High Similarity	NPC185536
0.9054	High Similarity	NPC230704
0.9054	High Similarity	NPC104387
0.9054	High Similarity	NPC288035
0.9054	High Similarity	NPC178383
0.9054	High Similarity	NPC212879
0.9054	High Similarity	NPC162742
0.9041	High Similarity	NPC474140
0.9028	High Similarity	NPC45296
0.9	High Similarity	NPC201273
0.9	High Similarity	NPC24277
0.8987	High Similarity	NPC209802
0.8987	High Similarity	NPC475798
0.8987	High Similarity	NPC124172
0.8987	High Similarity	NPC127606
0.8987	High Similarity	NPC478102
0.8974	High Similarity	NPC30166
0.8974	High Similarity	NPC470049
0.8974	High Similarity	NPC248886
0.8947	High Similarity	NPC477819
0.8947	High Similarity	NPC477817
0.8947	High Similarity	NPC473943
0.8947	High Similarity	NPC186191
0.8947	High Similarity	NPC301707
0.8947	High Similarity	NPC474216
0.8947	High Similarity	NPC477522
0.8947	High Similarity	NPC300499
0.8947	High Similarity	NPC87604
0.8947	High Similarity	NPC205455
0.8933	High Similarity	NPC93662
0.8933	High Similarity	NPC91573
0.8933	High Similarity	NPC278091
0.8933	High Similarity	NPC113733
0.8933	High Similarity	NPC470362
0.8933	High Similarity	NPC78067
0.8919	High Similarity	NPC145552
0.8919	High Similarity	NPC5046
0.8919	High Similarity	NPC196358
0.8919	High Similarity	NPC100334
0.8919	High Similarity	NPC192638
0.8919	High Similarity	NPC49168
0.8919	High Similarity	NPC254509
0.8919	High Similarity	NPC62657
0.8919	High Similarity	NPC472503
0.8919	High Similarity	NPC308440
0.8919	High Similarity	NPC25511
0.8904	High Similarity	NPC167706
0.8861	High Similarity	NPC82623
0.8861	High Similarity	NPC134481
0.8861	High Similarity	NPC470558
0.8846	High Similarity	NPC470383
0.8831	High Similarity	NPC109546
0.8831	High Similarity	NPC81306
0.8831	High Similarity	NPC143182
0.8831	High Similarity	NPC84694
0.8831	High Similarity	NPC328714
0.8831	High Similarity	NPC28862
0.8831	High Similarity	NPC47982
0.8816	High Similarity	NPC202540
0.8816	High Similarity	NPC212241
0.8816	High Similarity	NPC470758
0.8816	High Similarity	NPC257191
0.8816	High Similarity	NPC248830
0.8816	High Similarity	NPC157996
0.8816	High Similarity	NPC119355
0.8816	High Similarity	NPC34019
0.8816	High Similarity	NPC101475
0.8816	High Similarity	NPC40394
0.8816	High Similarity	NPC34177
0.8816	High Similarity	NPC331618
0.8816	High Similarity	NPC138502
0.8816	High Similarity	NPC470711
0.8816	High Similarity	NPC472805
0.8816	High Similarity	NPC90979
0.88	High Similarity	NPC103822
0.88	High Similarity	NPC200243
0.88	High Similarity	NPC291503
0.8784	High Similarity	NPC201373
0.8784	High Similarity	NPC182717
0.8784	High Similarity	NPC195489
0.878	High Similarity	NPC67872
0.8765	High Similarity	NPC139724
0.8765	High Similarity	NPC269058
0.8765	High Similarity	NPC6605
0.8765	High Similarity	NPC71520
0.875	High Similarity	NPC474493
0.875	High Similarity	NPC160209
0.875	High Similarity	NPC470077
0.8734	High Similarity	NPC201852
0.8734	High Similarity	NPC470614
0.8734	High Similarity	NPC1272
0.8734	High Similarity	NPC49964
0.8734	High Similarity	NPC101462
0.8734	High Similarity	NPC20853
0.8734	High Similarity	NPC87489
0.8734	High Similarity	NPC202389
0.8718	High Similarity	NPC71535
0.8718	High Similarity	NPC209944
0.8718	High Similarity	NPC234193
0.8718	High Similarity	NPC26117
0.8718	High Similarity	NPC164840
0.8718	High Similarity	NPC241290
0.8718	High Similarity	NPC475679
0.8718	High Similarity	NPC78545
0.8701	High Similarity	NPC18603
0.8701	High Similarity	NPC474989
0.8701	High Similarity	NPC31828
0.8701	High Similarity	NPC42853
0.8701	High Similarity	NPC158662
0.8701	High Similarity	NPC102708
0.8701	High Similarity	NPC11908
0.8701	High Similarity	NPC470396
0.8701	High Similarity	NPC76931
0.8701	High Similarity	NPC196753
0.8701	High Similarity	NPC472342
0.8701	High Similarity	NPC22955
0.8701	High Similarity	NPC477514
0.8701	High Similarity	NPC318136
0.8701	High Similarity	NPC230295
0.8701	High Similarity	NPC307965
0.8701	High Similarity	NPC98386
0.8701	High Similarity	NPC253807
0.8701	High Similarity	NPC99168
0.8684	High Similarity	NPC106432
0.8684	High Similarity	NPC38141
0.8684	High Similarity	NPC470749
0.8684	High Similarity	NPC247325
0.8684	High Similarity	NPC290598
0.8684	High Similarity	NPC27765
0.8684	High Similarity	NPC244488
0.8684	High Similarity	NPC265328
0.8684	High Similarity	NPC96319
0.8684	High Similarity	NPC120098
0.8684	High Similarity	NPC122418
0.8684	High Similarity	NPC30590

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 NPC167037 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1660
0.2-0.3	4467
0.3-0.4	2038
0.4-0.5	406
0.5-0.6	146
0.6-0.7	173
0.7-0.8	92
0.8-0.85	12
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.973	High Similarity	NPD7525	Registered
0.9054	High Similarity	NPD6942	Approved
0.9054	High Similarity	NPD7339	Approved
0.8684	High Similarity	NPD3701	Clinical (unspecified phase)
0.859	High Similarity	NPD7645	Phase 2
0.8421	Intermediate Similarity	NPD6926	Approved
0.8421	Intermediate Similarity	NPD6924	Approved
0.8293	Intermediate Similarity	NPD4786	Approved
0.8235	Intermediate Similarity	NPD5328	Approved
0.8205	Intermediate Similarity	NPD6933	Approved
0.8158	Intermediate Similarity	NPD4243	Approved
0.8158	Intermediate Similarity	NPD7151	Approved
0.8158	Intermediate Similarity	NPD7150	Approved
0.8158	Intermediate Similarity	NPD7152	Approved
0.8133	Intermediate Similarity	NPD6923	Approved
0.8133	Intermediate Similarity	NPD6922	Approved
0.8095	Intermediate Similarity	NPD3618	Phase 1
0.8049	Intermediate Similarity	NPD3667	Approved
0.8046	Intermediate Similarity	NPD6079	Approved
0.8026	Intermediate Similarity	NPD7143	Approved
0.8026	Intermediate Similarity	NPD7144	Approved
0.8025	Intermediate Similarity	NPD7509	Discontinued
0.7976	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD4202	Approved
0.7949	Intermediate Similarity	NPD4785	Approved
0.7949	Intermediate Similarity	NPD4784	Approved
0.7901	Intermediate Similarity	NPD6929	Approved
0.7805	Intermediate Similarity	NPD6931	Approved
0.7805	Intermediate Similarity	NPD4748	Discontinued
0.7805	Intermediate Similarity	NPD6930	Phase 2
0.7791	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6932	Approved
0.7654	Intermediate Similarity	NPD5776	Phase 2
0.7654	Intermediate Similarity	NPD6925	Approved
0.7647	Intermediate Similarity	NPD3133	Approved
0.7647	Intermediate Similarity	NPD3665	Phase 1
0.7647	Intermediate Similarity	NPD3666	Approved
0.7647	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD4190	Phase 3
0.7625	Intermediate Similarity	NPD5275	Approved
0.7609	Intermediate Similarity	NPD4755	Approved
0.7561	Intermediate Similarity	NPD7145	Approved
0.7556	Intermediate Similarity	NPD6399	Phase 3
0.7529	Intermediate Similarity	NPD6695	Phase 3
0.7527	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD5222	Approved
0.75	Intermediate Similarity	NPD4697	Phase 3
0.75	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5221	Approved
0.747	Intermediate Similarity	NPD4195	Approved
0.747	Intermediate Similarity	NPD6683	Phase 2
0.7447	Intermediate Similarity	NPD7640	Approved
0.7447	Intermediate Similarity	NPD7639	Approved
0.7447	Intermediate Similarity	NPD5286	Approved
0.7447	Intermediate Similarity	NPD4700	Approved
0.7447	Intermediate Similarity	NPD4696	Approved
0.7447	Intermediate Similarity	NPD5285	Approved
0.7444	Intermediate Similarity	NPD7515	Phase 2
0.7444	Intermediate Similarity	NPD8034	Phase 2
0.7444	Intermediate Similarity	NPD8035	Phase 2
0.7419	Intermediate Similarity	NPD5173	Approved
0.7381	Intermediate Similarity	NPD7514	Phase 3
0.7368	Intermediate Similarity	NPD5223	Approved
0.7356	Intermediate Similarity	NPD6893	Approved
0.7349	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4787	Phase 1
0.7326	Intermediate Similarity	NPD4788	Approved
0.7294	Intermediate Similarity	NPD6902	Approved
0.7292	Intermediate Similarity	NPD5225	Approved
0.7292	Intermediate Similarity	NPD5226	Approved
0.7292	Intermediate Similarity	NPD4633	Approved
0.7292	Intermediate Similarity	NPD5224	Approved
0.7292	Intermediate Similarity	NPD5211	Phase 2
0.7273	Intermediate Similarity	NPD5279	Phase 3
0.725	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7128	Approved
0.7245	Intermediate Similarity	NPD6675	Approved
0.7245	Intermediate Similarity	NPD6402	Approved
0.7245	Intermediate Similarity	NPD5739	Approved
0.7241	Intermediate Similarity	NPD3668	Phase 3
0.7229	Intermediate Similarity	NPD6116	Phase 1
0.7222	Intermediate Similarity	NPD4753	Phase 2
0.7216	Intermediate Similarity	NPD4754	Approved
0.7216	Intermediate Similarity	NPD5175	Approved
0.7216	Intermediate Similarity	NPD5174	Approved
0.7209	Intermediate Similarity	NPD4221	Approved
0.7209	Intermediate Similarity	NPD4223	Phase 3
0.7195	Intermediate Similarity	NPD8264	Approved
0.7191	Intermediate Similarity	NPD7524	Approved
0.7191	Intermediate Similarity	NPD7750	Discontinued
0.7176	Intermediate Similarity	NPD7332	Phase 2
0.7159	Intermediate Similarity	NPD5329	Approved
0.7158	Intermediate Similarity	NPD5290	Discontinued
0.7143	Intermediate Similarity	NPD5141	Approved
0.7108	Intermediate Similarity	NPD6117	Approved
0.71	Intermediate Similarity	NPD6881	Approved
0.71	Intermediate Similarity	NPD7320	Approved
0.71	Intermediate Similarity	NPD6899	Approved
0.7097	Intermediate Similarity	NPD7748	Approved
0.7093	Intermediate Similarity	NPD6898	Phase 1
0.7073	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4767	Approved
0.7071	Intermediate Similarity	NPD4768	Approved
0.7053	Intermediate Similarity	NPD7902	Approved
0.7045	Intermediate Similarity	NPD4197	Approved
0.703	Intermediate Similarity	NPD6373	Approved
0.703	Intermediate Similarity	NPD6372	Approved
0.7	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5701	Approved
0.7	Intermediate Similarity	NPD5697	Approved
0.7	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7102	Approved
0.6961	Remote Similarity	NPD6883	Approved
0.6961	Remote Similarity	NPD7290	Approved
0.6941	Remote Similarity	NPD6115	Approved
0.6941	Remote Similarity	NPD6114	Approved
0.6941	Remote Similarity	NPD6697	Approved
0.6941	Remote Similarity	NPD6118	Approved
0.6931	Remote Similarity	NPD4729	Approved
0.6931	Remote Similarity	NPD6011	Approved
0.6931	Remote Similarity	NPD4730	Approved
0.6931	Remote Similarity	NPD5128	Approved
0.6923	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6869	Approved
0.6893	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6649	Approved
0.6893	Remote Similarity	NPD6650	Approved
0.6893	Remote Similarity	NPD8130	Phase 1
0.6893	Remote Similarity	NPD6847	Approved
0.6893	Remote Similarity	NPD6617	Approved
0.6889	Remote Similarity	NPD6684	Approved
0.6889	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4689	Approved
0.6889	Remote Similarity	NPD4693	Phase 3
0.6889	Remote Similarity	NPD4138	Approved
0.6889	Remote Similarity	NPD7521	Approved
0.6889	Remote Similarity	NPD5330	Approved
0.6889	Remote Similarity	NPD5205	Approved
0.6889	Remote Similarity	NPD7146	Approved
0.6889	Remote Similarity	NPD4688	Approved
0.6889	Remote Similarity	NPD6409	Approved
0.6889	Remote Similarity	NPD7334	Approved
0.6889	Remote Similarity	NPD4690	Approved
0.6882	Remote Similarity	NPD7087	Discontinued
0.6875	Remote Similarity	NPD6084	Phase 2
0.6875	Remote Similarity	NPD6083	Phase 2
0.6863	Remote Similarity	NPD6013	Approved
0.6863	Remote Similarity	NPD6014	Approved
0.6863	Remote Similarity	NPD6012	Approved
0.6848	Remote Similarity	NPD6051	Approved
0.6842	Remote Similarity	NPD4629	Approved
0.6842	Remote Similarity	NPD5210	Approved
0.6827	Remote Similarity	NPD8297	Approved
0.6827	Remote Similarity	NPD6882	Approved
0.6796	Remote Similarity	NPD5250	Approved
0.6796	Remote Similarity	NPD5135	Approved
0.6796	Remote Similarity	NPD5249	Phase 3
0.6796	Remote Similarity	NPD5251	Approved
0.6796	Remote Similarity	NPD5169	Approved
0.6796	Remote Similarity	NPD5248	Approved
0.6796	Remote Similarity	NPD4634	Approved
0.6796	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5247	Approved
0.6786	Remote Similarity	NPD3703	Phase 2
0.6782	Remote Similarity	NPD6928	Phase 2
0.6768	Remote Similarity	NPD7632	Discontinued
0.6765	Remote Similarity	NPD5168	Approved
0.6753	Remote Similarity	NPD368	Approved
0.6744	Remote Similarity	NPD3617	Approved
0.6739	Remote Similarity	NPD5737	Approved
0.6739	Remote Similarity	NPD6903	Approved
0.6739	Remote Similarity	NPD4722	Approved
0.6739	Remote Similarity	NPD4723	Approved
0.6739	Remote Similarity	NPD6672	Approved
0.6737	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7900	Approved
0.6731	Remote Similarity	NPD5216	Approved
0.6731	Remote Similarity	NPD5215	Approved
0.6731	Remote Similarity	NPD5127	Approved
0.6731	Remote Similarity	NPD5217	Approved
0.6707	Remote Similarity	NPD4244	Approved
0.6707	Remote Similarity	NPD4245	Approved
0.6707	Remote Similarity	NPD4789	Approved
0.6703	Remote Similarity	NPD5280	Approved
0.6703	Remote Similarity	NPD5690	Phase 2
0.6703	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD5360	Phase 3
0.6667	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7327	Approved
0.6606	Remote Similarity	NPD7516	Approved
0.6604	Remote Similarity	NPD4632	Approved
0.6585	Remote Similarity	NPD3698	Phase 2
0.6545	Remote Similarity	NPD8294	Approved
0.6545	Remote Similarity	NPD8377	Approved
0.6542	Remote Similarity	NPD5167	Approved
0.6526	Remote Similarity	NPD5281	Approved
0.6526	Remote Similarity	NPD7637	Suspended

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