NPASS Compound

Structure

CID218616 OpenBabel06191716012D 32 35 0 0 1 0 0 0 0 0999 V2000 -3.0180 -2.8855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7662 -6.4083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0437 -5.7578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0120 2.3003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0398 2.3003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 -0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4465 0.4021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6839 0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7169 -4.3305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4165 -3.4059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3381 -0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3679 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6679 -4.5327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5259 -0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7666 -0.1857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0670 -2.6834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7666 -1.7588 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8420 -1.4583 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6839 0.9722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8420 -0.4861 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3679 0.9722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9683 -5.4573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5259 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8420 -0.4861 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 4.2098 1.4583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9193 -5.6595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 2 0 0 0 0 2 26 1 0 0 0 0 3 26 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 16 2 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 24 1 0 0 0 0 13 18 1 0 0 0 0 13 21 1 0 0 0 0 14 19 1 0 0 0 0 14 23 1 0 0 0 0 15 17 1 0 0 0 0 15 25 1 0 0 0 0 16 26 1 0 0 0 0 17 28 1 0 0 0 0 18 29 1 0 0 0 0 19 30 1 0 0 0 0 21 20 1 1 0 0 0 21 22 1 0 0 0 0 22 29 1 6 0 0 0 23 27 1 0 0 0 0 23 28 1 1 0 0 0 24 28 1 1 0 0 0 24 30 1 0 0 0 0 25 27 1 0 0 0 0 25 31 1 1 0 0 0 26 32 1 0 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:	442.38
Volume:	505.518
LogP:	5.664
LogD:	5.132
LogS:	-5.236
# Rotatable Bonds:	4
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	4.855
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:	-4.916
MDCK Permeability:	2.407652027613949e-05
Pgp-inhibitor:	0.044
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.799
30% Bioavailability (F30%):	0.084

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	92.97501373291016%
Volume Distribution (VD):	1.12
Pgp-substrate:	3.5197079181671143%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.501
CYP2C19-inhibitor:	0.13
CYP2C19-substrate:	0.922
CYP2C9-inhibitor:	0.26
CYP2C9-substrate:	0.738
CYP2D6-inhibitor:	0.151
CYP2D6-substrate:	0.882
CYP3A4-inhibitor:	0.488
CYP3A4-substrate:	0.348

ADMET: Excretion

Clearance (CL):	4.269
Half-life (T1/2):	0.139

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.121
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.2
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.637
Carcinogencity:	0.012
Eye Corrosion:	0.04
Eye Irritation:	0.271
Respiratory Toxicity:	0.607

Download Data

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

Natural Product: NPC218616

Natural Product ID:	NPC218616
*Common Name:**	(23E)-Dammara-20,23-Dien-3Beta,25-Diol
IUPAC Name:	(3S,5R,8R,9R,10R,13R,14R,17S)-17-[(4E)-6-hydroxy-6-methylhepta-1,4-dien-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms:
Standard InCHIKey:	HSBKLMIYIQJQRR-IHSJTJJSSA-N
Standard InCHI:	InChI=1S/C30H50O2/c1-20(10-9-16-26(2,3)32)21-13-18-29(7)22(21)11-12-24-28(6)17-15-25(31)27(4,5)23(28)14-19-30(24,29)8/h9,16,21-25,31-32H,1,10-15,17-19H2,2-8H3/b16-9+/t21-,22-,23+,24-,25+,28+,29-,30-/m1/s1
SMILES:	C=C(C/C=C/C(C)(C)O)[C@H]1CC[C@]2(C)[C@@H]1CC[C@@H]1[C@@]3(C)CC[C@@H](C(C)(C)[C@@H]3CC[C@@]21C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL39909
PubChem CID:	44285137
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
NPO2717	Vatica cinerea	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608862]
NPO11629	Brassica nigra	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21861458]
NPO11629	Brassica nigra	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11629	Brassica nigra	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15577	Volvariella volvacea	Species	Pluteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19655	Larix sukaczewii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15940	Pinus gerardiana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18201	Gonimbrasia belina	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2717	Vatica cinerea	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11629	Brassica nigra	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18469	Anochetus mayri	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19200	Rolandra fruticosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19109	Cetraria sanguinea	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15577	Volvariella volvacea	Species	Pluteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18798	Parmelia perlata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18546	Senna longiracemosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	1
IC50	2
Others	2

Activity Type	# Activity
Organism	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	0.8	ug.mL-1	PMID[469872]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	10.0	mg.kg-1	PMID[469872]
NPT27	Others	Unspecified		CC50	=	30300.0	nM	PMID[469873]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	22600.0	nM	PMID[469873]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	1.3	n.a.	PMID[469873]

☑ 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 NPC218616 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	163
0.1-0.2	1332
0.2-0.3	5655
0.3-0.4	15649
0.4-0.5	8168
0.5-0.6	5618
0.6-0.7	4252
0.7-0.8	1444
0.8-0.85	248
0.85-0.9	130
0.9-0.95	34
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC296701
0.9615	High Similarity	NPC82623
0.9487	High Similarity	NPC87489
0.9487	High Similarity	NPC49964
0.9474	High Similarity	NPC285761
0.9367	High Similarity	NPC134481
0.9367	High Similarity	NPC470558
0.9359	High Similarity	NPC264245
0.9351	High Similarity	NPC30986
0.9351	High Similarity	NPC209430
0.9351	High Similarity	NPC80530
0.9351	High Similarity	NPC273410
0.9342	High Similarity	NPC470711
0.9342	High Similarity	NPC470758
0.9259	High Similarity	NPC261266
0.925	High Similarity	NPC470077
0.925	High Similarity	NPC205845
0.925	High Similarity	NPC231310
0.9231	High Similarity	NPC322313
0.9231	High Similarity	NPC241290
0.9231	High Similarity	NPC102253
0.9231	High Similarity	NPC209944
0.9231	High Similarity	NPC164840
0.9231	High Similarity	NPC236237
0.9231	High Similarity	NPC13554
0.9231	High Similarity	NPC234193
0.9221	High Similarity	NPC11908
0.9221	High Similarity	NPC244385
0.9221	High Similarity	NPC167037
0.9221	High Similarity	NPC6978
0.9221	High Similarity	NPC138621
0.9211	High Similarity	NPC237460
0.9211	High Similarity	NPC470749
0.9136	High Similarity	NPC274448
0.9136	High Similarity	NPC318390
0.9136	High Similarity	NPC470360
0.9114	High Similarity	NPC47761
0.9103	High Similarity	NPC109546
0.9103	High Similarity	NPC143182
0.9103	High Similarity	NPC84694
0.9103	High Similarity	NPC28862
0.9103	High Similarity	NPC47982
0.9103	High Similarity	NPC81306
0.9079	High Similarity	NPC185536
0.9036	High Similarity	NPC133588
0.9024	High Similarity	NPC139724
0.9024	High Similarity	NPC6391
0.9024	High Similarity	NPC299068
0.9012	High Similarity	NPC474047
0.9012	High Similarity	NPC238485
0.9	High Similarity	NPC470049
0.9	High Similarity	NPC202389
0.9	High Similarity	NPC50964
0.9	High Similarity	NPC101462
0.8974	High Similarity	NPC301707
0.8974	High Similarity	NPC472342
0.8974	High Similarity	NPC474216
0.8974	High Similarity	NPC65897
0.8974	High Similarity	NPC302041
0.8974	High Similarity	NPC85346
0.8961	High Similarity	NPC244488
0.8961	High Similarity	NPC134330
0.8961	High Similarity	NPC129165
0.8961	High Similarity	NPC189883
0.8961	High Similarity	NPC247325
0.8947	High Similarity	NPC201048
0.8947	High Similarity	NPC476366
0.8916	High Similarity	NPC149224
0.8902	High Similarity	NPC157257
0.8889	High Similarity	NPC317458
0.8889	High Similarity	NPC474634
0.8889	High Similarity	NPC477818
0.8889	High Similarity	NPC207013
0.8889	High Similarity	NPC475789
0.8875	High Similarity	NPC209620
0.8875	High Similarity	NPC23852
0.8861	High Similarity	NPC1319
0.8846	High Similarity	NPC331618
0.8846	High Similarity	NPC119355
0.8846	High Similarity	NPC318495
0.8846	High Similarity	NPC91594
0.8846	High Similarity	NPC155986
0.8846	High Similarity	NPC198968
0.8846	High Similarity	NPC212241
0.8846	High Similarity	NPC257191
0.8846	High Similarity	NPC248830
0.8846	High Similarity	NPC214570
0.8831	High Similarity	NPC141071
0.8831	High Similarity	NPC3403
0.8831	High Similarity	NPC471723
0.8831	High Similarity	NPC257347
0.8824	High Similarity	NPC3345
0.8824	High Similarity	NPC80561
0.8824	High Similarity	NPC329596
0.8824	High Similarity	NPC295668
0.8824	High Similarity	NPC11216
0.8824	High Similarity	NPC204188
0.8824	High Similarity	NPC291484
0.881	High Similarity	NPC67872
0.878	High Similarity	NPC15534
0.878	High Similarity	NPC474493
0.878	High Similarity	NPC185568
0.8765	High Similarity	NPC189972
0.8765	High Similarity	NPC30166
0.875	High Similarity	NPC295131
0.875	High Similarity	NPC236112
0.8734	High Similarity	NPC472501
0.8734	High Similarity	NPC473943
0.8734	High Similarity	NPC275910
0.8734	High Similarity	NPC312328
0.8721	High Similarity	NPC275671
0.8721	High Similarity	NPC41554
0.8721	High Similarity	NPC97404
0.8718	High Similarity	NPC265588
0.8718	High Similarity	NPC300324
0.8718	High Similarity	NPC113733
0.8718	High Similarity	NPC73875
0.8718	High Similarity	NPC46160
0.8718	High Similarity	NPC321016
0.8718	High Similarity	NPC321381
0.8718	High Similarity	NPC240604
0.8718	High Similarity	NPC107059
0.8718	High Similarity	NPC91573
0.8718	High Similarity	NPC202642
0.8718	High Similarity	NPC470362
0.8706	High Similarity	NPC101886
0.8706	High Similarity	NPC470361
0.8701	High Similarity	NPC469534
0.8701	High Similarity	NPC469533
0.8701	High Similarity	NPC469593
0.8701	High Similarity	NPC476736
0.869	High Similarity	NPC470620
0.8684	High Similarity	NPC111234
0.8684	High Similarity	NPC167706
0.8675	High Similarity	NPC266511
0.8659	High Similarity	NPC113978
0.8659	High Similarity	NPC470384
0.8659	High Similarity	NPC110778
0.8659	High Similarity	NPC193870
0.8659	High Similarity	NPC141941
0.8642	High Similarity	NPC476646
0.8642	High Similarity	NPC249423
0.8642	High Similarity	NPC474531
0.8642	High Similarity	NPC474683
0.8642	High Similarity	NPC474731
0.8642	High Similarity	NPC474752
0.8642	High Similarity	NPC7505
0.8642	High Similarity	NPC82986
0.8642	High Similarity	NPC474759
0.8625	High Similarity	NPC328714
0.8625	High Similarity	NPC472463
0.8608	High Similarity	NPC138502
0.8608	High Similarity	NPC260301
0.8608	High Similarity	NPC307336
0.859	High Similarity	NPC230704
0.859	High Similarity	NPC178383
0.859	High Similarity	NPC322353
0.859	High Similarity	NPC285893
0.859	High Similarity	NPC70982
0.859	High Similarity	NPC240235
0.859	High Similarity	NPC304309
0.859	High Similarity	NPC230301
0.859	High Similarity	NPC162742
0.859	High Similarity	NPC134847
0.859	High Similarity	NPC231256
0.859	High Similarity	NPC104387
0.859	High Similarity	NPC288035
0.859	High Similarity	NPC212879
0.859	High Similarity	NPC22105
0.859	High Similarity	NPC118508
0.859	High Similarity	NPC32832
0.859	High Similarity	NPC28657
0.859	High Similarity	NPC103822
0.859	High Similarity	NPC136188
0.859	High Similarity	NPC121744
0.8588	High Similarity	NPC471952
0.8588	High Similarity	NPC212596
0.8588	High Similarity	NPC474668
0.8588	High Similarity	NPC4574
0.8571	High Similarity	NPC201273
0.8571	High Similarity	NPC152808
0.8571	High Similarity	NPC182717
0.8571	High Similarity	NPC474743
0.8571	High Similarity	NPC293287
0.8571	High Similarity	NPC6605
0.8554	High Similarity	NPC209802
0.8554	High Similarity	NPC475798
0.8554	High Similarity	NPC127606
0.8553	High Similarity	NPC45296
0.8537	High Similarity	NPC248886
0.8537	High Similarity	NPC155521
0.8523	High Similarity	NPC144202
0.8519	High Similarity	NPC96362
0.8506	High Similarity	NPC110923
0.8506	High Similarity	NPC74296
0.8506	High Similarity	NPC475806
0.85	High Similarity	NPC167891
0.85	High Similarity	NPC472500
0.85	High Similarity	NPC42853
0.85	High Similarity	NPC87604

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 NPC218616 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1482
0.2-0.3	4281
0.3-0.4	2256
0.4-0.5	525
0.5-0.6	170
0.6-0.7	191
0.7-0.8	78
0.8-0.85	6
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD7525	Registered
0.859	High Similarity	NPD6942	Approved
0.859	High Similarity	NPD7339	Approved
0.8256	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD6926	Approved
0.8228	Intermediate Similarity	NPD6924	Approved
0.8171	Intermediate Similarity	NPD7645	Phase 2
0.8072	Intermediate Similarity	NPD7514	Phase 3
0.8072	Intermediate Similarity	NPD6930	Phase 2
0.8072	Intermediate Similarity	NPD6931	Approved
0.8049	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD6933	Approved
0.8	Intermediate Similarity	NPD4785	Approved
0.8	Intermediate Similarity	NPD4784	Approved
0.7975	Intermediate Similarity	NPD7150	Approved
0.7975	Intermediate Similarity	NPD7152	Approved
0.7975	Intermediate Similarity	NPD4243	Approved
0.7975	Intermediate Similarity	NPD7151	Approved
0.7952	Intermediate Similarity	NPD6929	Approved
0.7907	Intermediate Similarity	NPD4786	Approved
0.7889	Intermediate Similarity	NPD6079	Approved
0.7865	Intermediate Similarity	NPD5328	Approved
0.7857	Intermediate Similarity	NPD7332	Phase 2
0.7848	Intermediate Similarity	NPD7143	Approved
0.7848	Intermediate Similarity	NPD7144	Approved
0.7831	Intermediate Similarity	NPD7145	Approved
0.7791	Intermediate Similarity	NPD6695	Phase 3
0.7765	Intermediate Similarity	NPD6902	Approved
0.7727	Intermediate Similarity	NPD3618	Phase 1
0.7722	Intermediate Similarity	NPD6922	Approved
0.7722	Intermediate Similarity	NPD6923	Approved
0.7711	Intermediate Similarity	NPD6932	Approved
0.7711	Intermediate Similarity	NPD5776	Phase 2
0.7711	Intermediate Similarity	NPD6925	Approved
0.7701	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7640	Approved
0.7684	Intermediate Similarity	NPD7639	Approved
0.7683	Intermediate Similarity	NPD8264	Approved
0.7674	Intermediate Similarity	NPD3667	Approved
0.7647	Intermediate Similarity	NPD7509	Discontinued
0.7647	Intermediate Similarity	NPD4748	Discontinued
0.7614	Intermediate Similarity	NPD6893	Approved
0.7614	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD4202	Approved
0.7579	Intermediate Similarity	NPD7638	Approved
0.7529	Intermediate Similarity	NPD4195	Approved
0.7526	Intermediate Similarity	NPD5211	Phase 2
0.75	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4190	Phase 3
0.747	Intermediate Similarity	NPD5275	Approved
0.7444	Intermediate Similarity	NPD7750	Discontinued
0.7444	Intermediate Similarity	NPD7524	Approved
0.7374	Intermediate Similarity	NPD5141	Approved
0.7368	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5221	Approved
0.7368	Intermediate Similarity	NPD5222	Approved
0.7356	Intermediate Similarity	NPD6898	Phase 1
0.7326	Intermediate Similarity	NPD6683	Phase 2
0.732	Intermediate Similarity	NPD5285	Approved
0.732	Intermediate Similarity	NPD5286	Approved
0.732	Intermediate Similarity	NPD4696	Approved
0.7303	Intermediate Similarity	NPD3666	Approved
0.7303	Intermediate Similarity	NPD3133	Approved
0.7303	Intermediate Similarity	NPD3665	Phase 1
0.7292	Intermediate Similarity	NPD4755	Approved
0.7292	Intermediate Similarity	NPD5173	Approved
0.7245	Intermediate Similarity	NPD5223	Approved
0.7195	Intermediate Similarity	NPD4787	Phase 1
0.7191	Intermediate Similarity	NPD4788	Approved
0.7188	Intermediate Similarity	NPD4697	Phase 3
0.7172	Intermediate Similarity	NPD4633	Approved
0.7172	Intermediate Similarity	NPD5225	Approved
0.7172	Intermediate Similarity	NPD5226	Approved
0.7172	Intermediate Similarity	NPD5224	Approved
0.7143	Intermediate Similarity	NPD4700	Approved
0.7128	Intermediate Similarity	NPD7087	Discontinued
0.7128	Intermediate Similarity	NPD7515	Phase 2
0.71	Intermediate Similarity	NPD5175	Approved
0.71	Intermediate Similarity	NPD5174	Approved
0.7097	Intermediate Similarity	NPD4753	Phase 2
0.7097	Intermediate Similarity	NPD6051	Approved
0.7079	Intermediate Similarity	NPD4223	Phase 3
0.7079	Intermediate Similarity	NPD4221	Approved
0.7053	Intermediate Similarity	NPD6399	Phase 3
0.7051	Intermediate Similarity	NPD368	Approved
0.7041	Intermediate Similarity	NPD5290	Discontinued
0.7033	Intermediate Similarity	NPD5329	Approved
0.7	Intermediate Similarity	NPD7632	Discontinued
0.699	Remote Similarity	NPD6881	Approved
0.699	Remote Similarity	NPD6899	Approved
0.6961	Remote Similarity	NPD5739	Approved
0.6961	Remote Similarity	NPD7128	Approved
0.6961	Remote Similarity	NPD6675	Approved
0.6961	Remote Similarity	NPD6402	Approved
0.6957	Remote Similarity	NPD4623	Approved
0.6957	Remote Similarity	NPD5279	Phase 3
0.6957	Remote Similarity	NPD4519	Discontinued
0.6947	Remote Similarity	NPD8035	Phase 2
0.6947	Remote Similarity	NPD8034	Phase 2
0.6947	Remote Similarity	NPD7637	Suspended
0.6944	Remote Similarity	NPD7115	Discovery
0.6931	Remote Similarity	NPD4754	Approved
0.6923	Remote Similarity	NPD4197	Approved
0.6923	Remote Similarity	NPD3668	Phase 3
0.6907	Remote Similarity	NPD5210	Approved
0.6907	Remote Similarity	NPD4629	Approved
0.6905	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5697	Approved
0.6857	Remote Similarity	NPD6883	Approved
0.6857	Remote Similarity	NPD7290	Approved
0.6857	Remote Similarity	NPD7102	Approved
0.6827	Remote Similarity	NPD6011	Approved
0.6827	Remote Similarity	NPD7320	Approved
0.6827	Remote Similarity	NPD4729	Approved
0.6827	Remote Similarity	NPD4730	Approved
0.6818	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD7748	Approved
0.6796	Remote Similarity	NPD4768	Approved
0.6796	Remote Similarity	NPD4767	Approved
0.6792	Remote Similarity	NPD6617	Approved
0.6792	Remote Similarity	NPD6650	Approved
0.6792	Remote Similarity	NPD6869	Approved
0.6792	Remote Similarity	NPD8130	Phase 1
0.6792	Remote Similarity	NPD6649	Approved
0.6792	Remote Similarity	NPD6847	Approved
0.6782	Remote Similarity	NPD6117	Approved
0.6774	Remote Similarity	NPD4138	Approved
0.6774	Remote Similarity	NPD5690	Phase 2
0.6774	Remote Similarity	NPD4688	Approved
0.6774	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4690	Approved
0.6774	Remote Similarity	NPD5205	Approved
0.6774	Remote Similarity	NPD4693	Phase 3
0.6774	Remote Similarity	NPD4689	Approved
0.6768	Remote Similarity	NPD6084	Phase 2
0.6768	Remote Similarity	NPD6083	Phase 2
0.6762	Remote Similarity	NPD6373	Approved
0.6762	Remote Similarity	NPD6372	Approved
0.6762	Remote Similarity	NPD6013	Approved
0.6762	Remote Similarity	NPD6014	Approved
0.6762	Remote Similarity	NPD6012	Approved
0.6744	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4159	Approved
0.6731	Remote Similarity	NPD5701	Approved
0.6729	Remote Similarity	NPD8297	Approved
0.6729	Remote Similarity	NPD6882	Approved
0.6727	Remote Similarity	NPD7328	Approved
0.6727	Remote Similarity	NPD7327	Approved
0.6705	Remote Similarity	NPD6116	Phase 1
0.67	Remote Similarity	NPD4225	Approved
0.6698	Remote Similarity	NPD5251	Approved
0.6698	Remote Similarity	NPD5248	Approved
0.6698	Remote Similarity	NPD5249	Phase 3
0.6698	Remote Similarity	NPD4634	Approved
0.6698	Remote Similarity	NPD5247	Approved
0.6698	Remote Similarity	NPD5250	Approved
0.6698	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5135	Approved
0.6698	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD7136	Phase 2
0.6667	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5168	Approved
0.6636	Remote Similarity	NPD5216	Approved
0.6636	Remote Similarity	NPD5217	Approved
0.6636	Remote Similarity	NPD5215	Approved
0.6636	Remote Similarity	NPD5127	Approved
0.6636	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4723	Approved
0.6632	Remote Similarity	NPD4722	Approved
0.6632	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6697	Approved
0.6629	Remote Similarity	NPD6118	Approved
0.6629	Remote Similarity	NPD6115	Approved
0.6629	Remote Similarity	NPD6114	Approved
0.6607	Remote Similarity	NPD8377	Approved
0.6607	Remote Similarity	NPD8294	Approved
0.66	Remote Similarity	NPD7902	Approved
0.6596	Remote Similarity	NPD7334	Approved
0.6596	Remote Similarity	NPD5280	Approved
0.6596	Remote Similarity	NPD7521	Approved
0.6596	Remote Similarity	NPD5330	Approved
0.6596	Remote Similarity	NPD6409	Approved
0.6596	Remote Similarity	NPD7146	Approved
0.6596	Remote Similarity	NPD4694	Approved
0.6596	Remote Similarity	NPD6684	Approved
0.6549	Remote Similarity	NPD8296	Approved
0.6549	Remote Similarity	NPD8033	Approved
0.6549	Remote Similarity	NPD8335	Approved
0.6549	Remote Similarity	NPD8378	Approved
0.6549	Remote Similarity	NPD8380	Approved
0.6549	Remote Similarity	NPD8379	Approved
0.6548	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD5360	Phase 3
0.6514	Remote Similarity	NPD4632	Approved
0.6494	Remote Similarity	NPD342	Phase 1

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