NPASS Compound

Structure

CID268160 OpenBabel06191716072D 22 24 0 0 1 0 0 0 0 0999 V2000 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 -3.2321 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 5 10 1 0 0 0 0 5 11 1 0 0 0 0 6 9 1 0 0 0 0 6 14 1 0 0 0 0 7 8 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 19 1 0 0 0 0 12 21 1 0 0 0 0 13 18 1 0 0 0 0 14 15 2 0 0 0 0 14 18 1 0 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 19 1 1 0 0 0 17 20 1 0 0 0 0 19 3 1 6 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	338.478
LogP:	4.477
LogD:	3.805
LogS:	-4.142
# Rotatable Bonds:	2
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.843
Synthetic Accessibility Score:	3.759
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.648
MDCK Permeability:	2.0011582819279283e-05
Pgp-inhibitor:	0.25
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.982
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.224
Plasma Protein Binding (PPB):	97.38936614990234%
Volume Distribution (VD):	2.351
Pgp-substrate:	2.861624002456665%

ADMET: Metabolism

CYP1A2-inhibitor:	0.344
CYP1A2-substrate:	0.829
CYP2C19-inhibitor:	0.14
CYP2C19-substrate:	0.92
CYP2C9-inhibitor:	0.162
CYP2C9-substrate:	0.649
CYP2D6-inhibitor:	0.462
CYP2D6-substrate:	0.471
CYP3A4-inhibitor:	0.701
CYP3A4-substrate:	0.682

ADMET: Excretion

Clearance (CL):	13.062
Half-life (T1/2):	0.253

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.13
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.115
Rat Oral Acute Toxicity:	0.227
Maximum Recommended Daily Dose:	0.345
Skin Sensitization:	0.806
Carcinogencity:	0.141
Eye Corrosion:	0.004
Eye Irritation:	0.089
Respiratory Toxicity:	0.857

Download Data

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

Natural Product: NPC268160

Natural Product ID:	NPC268160
*Common Name:**	19-Hydroxytotarol
IUPAC Name:	(4bS,8S,8aR)-8-(hydroxymethyl)-4b,8-dimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-2-ol
Synonyms:	19-Hydroxy-Totarol
Standard InCHIKey:	NFEAIVZJRVEKFD-DFQSSKMNSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-13(2)18-14-6-9-17-19(3,12-21)10-5-11-20(17,4)15(14)7-8-16(18)22/h7-8,13,17,21-22H,5-6,9-12H2,1-4H3/t17-,19+,20+/m0/s1
SMILES:	CC(C)c1c2CC[C@H]3[C@](C)(CCC[C@]3(C)c2ccc1O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478771
PubChem CID:	15694357
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO9389	Swertia bimaculata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/cbdv.200490123]
NPO9389	Swertia bimaculata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)98635-7]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869194]
NPO6506	Cupaniopsis macropetala	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18163587]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18588343]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19331340]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27700077]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28225280]
NPO9921	Peyronellaea glomerata	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29738260]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31789520]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31804070]
NPO1849	Pleiospermium alatum	Species	Rutaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO1849	Pleiospermium alatum	Species	Rutaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO1849	Pleiospermium alatum	Species	Rutaceae	Eukaryota	n.a.	stem	n.a.	Database[Article]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15989	Rabdosia yuennanensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9921	Peyronellaea glomerata	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4452	Erythrina falcata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14606	Leucanthemella serotina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14265	Stokesia laevis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15179	Cocculus hirsutus	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO930	Psalliota campestris	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO22	Osmitopsis asteriscoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2771	Teucrium ramosissimum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14755	Ornithogalum montanum	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1849	Pleiospermium alatum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25110	Neomirandea angularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15989	Rabdosia yuennanensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9389	Swertia bimaculata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6506	Cupaniopsis macropetala	Species	Sapindaceae	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
Others	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	15.89	%	PMID[490411]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	20.52	%	PMID[490411]

☑ 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 NPC268160 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	272
0.1-0.2	1513
0.2-0.3	3286
0.3-0.4	9596
0.4-0.5	9875
0.5-0.6	10060
0.6-0.7	6371
0.7-0.8	1458
0.8-0.85	153
0.85-0.9	74
0.9-0.95	23
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.9907	High Similarity	NPC147179
0.9815	High Similarity	NPC308828
0.9815	High Similarity	NPC219112
0.9722	High Similarity	NPC192948
0.9722	High Similarity	NPC35797
0.9636	High Similarity	NPC469609
0.9633	High Similarity	NPC308311
0.9633	High Similarity	NPC38893
0.9633	High Similarity	NPC477137
0.9623	High Similarity	NPC141782
0.9545	High Similarity	NPC172219
0.9545	High Similarity	NPC304510
0.9545	High Similarity	NPC477136
0.9459	High Similarity	NPC471671
0.9455	High Similarity	NPC92
0.9455	High Similarity	NPC469663
0.9375	High Similarity	NPC469644
0.9352	High Similarity	NPC260323
0.9352	High Similarity	NPC176279
0.9292	High Similarity	NPC135467
0.9292	High Similarity	NPC260832
0.9273	High Similarity	NPC195922
0.9266	High Similarity	NPC250323
0.9266	High Similarity	NPC228425
0.9259	High Similarity	NPC13482
0.9217	High Similarity	NPC471794
0.9196	High Similarity	NPC16030
0.9174	High Similarity	NPC95716
0.9138	High Similarity	NPC198014
0.913	High Similarity	NPC253627
0.9115	High Similarity	NPC164649
0.9115	High Similarity	NPC48342
0.9115	High Similarity	NPC154030
0.9107	High Similarity	NPC471668
0.9091	High Similarity	NPC46940
0.9083	High Similarity	NPC132720
0.9074	High Similarity	NPC11554
0.9043	High Similarity	NPC328504
0.9009	High Similarity	NPC715
0.9	High Similarity	NPC77772
0.9	High Similarity	NPC322753
0.8983	High Similarity	NPC87985
0.8981	High Similarity	NPC151477
0.8974	High Similarity	NPC471187
0.8938	High Similarity	NPC154511
0.8938	High Similarity	NPC247858
0.8938	High Similarity	NPC137496
0.8938	High Similarity	NPC474387
0.8938	High Similarity	NPC474358
0.8938	High Similarity	NPC257540
0.8929	High Similarity	NPC471534
0.8898	High Similarity	NPC181334
0.8889	High Similarity	NPC11250
0.887	High Similarity	NPC93071
0.887	High Similarity	NPC151197
0.887	High Similarity	NPC126002
0.885	High Similarity	NPC469719
0.8829	High Similarity	NPC266937
0.8829	High Similarity	NPC470770
0.8818	High Similarity	NPC58865
0.8803	High Similarity	NPC142198
0.8803	High Similarity	NPC77569
0.8796	High Similarity	NPC117115
0.8772	High Similarity	NPC141001
0.875	High Similarity	NPC177962
0.875	High Similarity	NPC71610
0.875	High Similarity	NPC62867
0.875	High Similarity	NPC321822
0.875	High Similarity	NPC325294
0.8729	High Similarity	NPC152946
0.8718	High Similarity	NPC259703
0.8718	High Similarity	NPC32322
0.8716	High Similarity	NPC21594
0.8716	High Similarity	NPC271274
0.8678	High Similarity	NPC471077
0.8667	High Similarity	NPC76119
0.8667	High Similarity	NPC137750
0.8667	High Similarity	NPC4286
0.8661	High Similarity	NPC151537
0.8649	High Similarity	NPC314187
0.8644	High Similarity	NPC249340
0.8644	High Similarity	NPC162935
0.8636	High Similarity	NPC472979
0.8636	High Similarity	NPC320439
0.8636	High Similarity	NPC27252
0.8632	High Similarity	NPC68339
0.8624	High Similarity	NPC243601
0.8598	High Similarity	NPC211885
0.8598	High Similarity	NPC225506
0.8595	High Similarity	NPC100414
0.8595	High Similarity	NPC43000
0.8584	High Similarity	NPC302371
0.8571	High Similarity	NPC176208
0.8571	High Similarity	NPC478058
0.8571	High Similarity	NPC121168
0.8571	High Similarity	NPC321402
0.8571	High Similarity	NPC71094
0.8571	High Similarity	NPC296683
0.8559	High Similarity	NPC64642
0.8559	High Similarity	NPC472982
0.8559	High Similarity	NPC262365
0.8559	High Similarity	NPC149455
0.8559	High Similarity	NPC241001
0.8547	High Similarity	NPC323074
0.8547	High Similarity	NPC42657
0.8534	High Similarity	NPC299180
0.8532	High Similarity	NPC475225
0.8525	High Similarity	NPC476536
0.8525	High Similarity	NPC108164
0.8522	High Similarity	NPC474486
0.8512	High Similarity	NPC124030
0.8509	High Similarity	NPC322239
0.8509	High Similarity	NPC317869
0.8505	High Similarity	NPC122005
0.8505	High Similarity	NPC128723
0.8505	High Similarity	NPC252821
0.8487	Intermediate Similarity	NPC475166
0.8487	Intermediate Similarity	NPC154696
0.8475	Intermediate Similarity	NPC190501
0.8475	Intermediate Similarity	NPC325544
0.8475	Intermediate Similarity	NPC99734
0.8475	Intermediate Similarity	NPC318581
0.8475	Intermediate Similarity	NPC318552
0.8475	Intermediate Similarity	NPC477037
0.8468	Intermediate Similarity	NPC472980
0.8462	Intermediate Similarity	NPC206
0.8455	Intermediate Similarity	NPC138942
0.844	Intermediate Similarity	NPC471228
0.844	Intermediate Similarity	NPC235762
0.844	Intermediate Similarity	NPC19856
0.844	Intermediate Similarity	NPC168829
0.8435	Intermediate Similarity	NPC107240
0.8421	Intermediate Similarity	NPC471179
0.8411	Intermediate Similarity	NPC77492
0.8407	Intermediate Similarity	NPC44732
0.84	Intermediate Similarity	NPC471851
0.8374	Intermediate Similarity	NPC30491
0.8374	Intermediate Similarity	NPC262936
0.8374	Intermediate Similarity	NPC186889
0.8364	Intermediate Similarity	NPC288411
0.8364	Intermediate Similarity	NPC238696
0.8364	Intermediate Similarity	NPC323810
0.8362	Intermediate Similarity	NPC84999
0.8362	Intermediate Similarity	NPC246760
0.8349	Intermediate Similarity	NPC252105
0.8349	Intermediate Similarity	NPC51015
0.8333	Intermediate Similarity	NPC308689
0.8333	Intermediate Similarity	NPC33675
0.8333	Intermediate Similarity	NPC92730
0.8333	Intermediate Similarity	NPC299762
0.8319	Intermediate Similarity	NPC478121
0.8319	Intermediate Similarity	NPC103916
0.8304	Intermediate Similarity	NPC66834
0.8291	Intermediate Similarity	NPC312105
0.8291	Intermediate Similarity	NPC261973
0.8288	Intermediate Similarity	NPC99557
0.8288	Intermediate Similarity	NPC47284
0.8288	Intermediate Similarity	NPC219286
0.8279	Intermediate Similarity	NPC265413
0.8279	Intermediate Similarity	NPC10154
0.8276	Intermediate Similarity	NPC249270
0.8276	Intermediate Similarity	NPC12656
0.8273	Intermediate Similarity	NPC269212
0.8268	Intermediate Similarity	NPC78307
0.8264	Intermediate Similarity	NPC297057
0.8261	Intermediate Similarity	NPC473521
0.8257	Intermediate Similarity	NPC72729
0.8257	Intermediate Similarity	NPC174911
0.8257	Intermediate Similarity	NPC294741
0.8254	Intermediate Similarity	NPC312341
0.8254	Intermediate Similarity	NPC476847
0.825	Intermediate Similarity	NPC129176
0.8241	Intermediate Similarity	NPC225464
0.8241	Intermediate Similarity	NPC79241
0.8241	Intermediate Similarity	NPC6597
0.824	Intermediate Similarity	NPC276238
0.8235	Intermediate Similarity	NPC176893
0.8226	Intermediate Similarity	NPC84672
0.8226	Intermediate Similarity	NPC69424
0.8226	Intermediate Similarity	NPC176130
0.8226	Intermediate Similarity	NPC78364
0.8224	Intermediate Similarity	NPC222146
0.8224	Intermediate Similarity	NPC144682
0.8224	Intermediate Similarity	NPC8392
0.8214	Intermediate Similarity	NPC155072
0.8214	Intermediate Similarity	NPC54765
0.8214	Intermediate Similarity	NPC53740
0.8203	Intermediate Similarity	NPC202225
0.8198	Intermediate Similarity	NPC272029
0.819	Intermediate Similarity	NPC321589
0.819	Intermediate Similarity	NPC117846
0.819	Intermediate Similarity	NPC263753
0.8189	Intermediate Similarity	NPC321086
0.8189	Intermediate Similarity	NPC85595
0.8182	Intermediate Similarity	NPC474115
0.8175	Intermediate Similarity	NPC196193
0.8175	Intermediate Similarity	NPC249425
0.8175	Intermediate Similarity	NPC472793
0.8174	Intermediate Similarity	NPC165770
0.8174	Intermediate Similarity	NPC4493

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 NPC268160 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	268
0.1-0.2	937
0.2-0.3	1297
0.3-0.4	2815
0.4-0.5	2045
0.5-0.6	1251
0.6-0.7	429
0.7-0.8	94
0.8-0.85	12
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9115	High Similarity	NPD3091	Approved
0.8803	High Similarity	NPD3092	Approved
0.8632	High Similarity	NPD3095	Discontinued
0.8512	High Similarity	NPD3094	Phase 2
0.8475	Intermediate Similarity	NPD3019	Approved
0.8475	Intermediate Similarity	NPD4059	Approved
0.8468	Intermediate Similarity	NPD2342	Discontinued
0.8421	Intermediate Similarity	NPD7635	Approved
0.8333	Intermediate Similarity	NPD3020	Approved
0.8319	Intermediate Similarity	NPD2932	Approved
0.8226	Intermediate Similarity	NPD5736	Approved
0.8224	Intermediate Similarity	NPD1809	Phase 2
0.8148	Intermediate Similarity	NPD288	Approved
0.8131	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8091	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD2860	Approved
0.8056	Intermediate Similarity	NPD2859	Approved
0.8056	Intermediate Similarity	NPD844	Approved
0.8049	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD845	Approved
0.8	Intermediate Similarity	NPD3021	Approved
0.8	Intermediate Similarity	NPD3022	Approved
0.7969	Intermediate Similarity	NPD6663	Approved
0.7963	Intermediate Similarity	NPD2933	Approved
0.7963	Intermediate Similarity	NPD2934	Approved
0.7934	Intermediate Similarity	NPD4093	Discontinued
0.7923	Intermediate Similarity	NPD4097	Suspended
0.7907	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD3620	Phase 2
0.7869	Intermediate Similarity	NPD2286	Discontinued
0.7869	Intermediate Similarity	NPD1751	Approved
0.7863	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD4624	Approved
0.7845	Intermediate Similarity	NPD4750	Phase 3
0.7805	Intermediate Similarity	NPD3023	Approved
0.7805	Intermediate Similarity	NPD3026	Approved
0.7803	Intermediate Similarity	NPD7743	Approved
0.7803	Intermediate Similarity	NPD7742	Approved
0.7787	Intermediate Similarity	NPD3025	Approved
0.7787	Intermediate Similarity	NPD3024	Approved
0.7769	Intermediate Similarity	NPD4140	Approved
0.776	Intermediate Similarity	NPD5327	Phase 3
0.7742	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD2605	Approved
0.7734	Intermediate Similarity	NPD2606	Approved
0.7731	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD4626	Approved
0.771	Intermediate Similarity	NPD5735	Approved
0.7674	Intermediate Similarity	NPD5156	Approved
0.7674	Intermediate Similarity	NPD5155	Approved
0.7656	Intermediate Similarity	NPD3636	Approved
0.7656	Intermediate Similarity	NPD3635	Approved
0.7656	Intermediate Similarity	NPD3637	Approved
0.7634	Intermediate Similarity	NPD4060	Phase 1
0.7632	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD3594	Approved
0.7597	Intermediate Similarity	NPD3595	Approved
0.7583	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD4589	Approved
0.7578	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2195	Approved
0.7578	Intermediate Similarity	NPD2194	Approved
0.7574	Intermediate Similarity	NPD3638	Discontinued
0.7544	Intermediate Similarity	NPD846	Approved
0.7544	Intermediate Similarity	NPD940	Approved
0.7542	Intermediate Similarity	NPD1792	Phase 2
0.7541	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD6353	Approved
0.75	Intermediate Similarity	NPD5691	Approved
0.7481	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD1201	Approved
0.7438	Intermediate Similarity	NPD2228	Approved
0.7438	Intermediate Similarity	NPD2229	Approved
0.7438	Intermediate Similarity	NPD2234	Approved
0.7422	Intermediate Similarity	NPD6696	Suspended
0.7419	Intermediate Similarity	NPD5303	Approved
0.7419	Intermediate Similarity	NPD5304	Approved
0.7405	Intermediate Similarity	NPD4625	Phase 3
0.7385	Intermediate Similarity	NPD2861	Phase 2
0.7377	Intermediate Similarity	NPD497	Approved
0.7364	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD4908	Phase 1
0.7304	Intermediate Similarity	NPD1242	Phase 1
0.7302	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD4725	Approved
0.7299	Intermediate Similarity	NPD4721	Approved
0.7299	Intermediate Similarity	NPD4726	Approved
0.7295	Intermediate Similarity	NPD498	Approved
0.7295	Intermediate Similarity	NPD495	Approved
0.7295	Intermediate Similarity	NPD496	Approved
0.729	Intermediate Similarity	NPD111	Approved
0.7288	Intermediate Similarity	NPD1444	Approved
0.7288	Intermediate Similarity	NPD1445	Approved
0.7287	Intermediate Similarity	NPD1283	Approved
0.728	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD8166	Discontinued
0.7266	Intermediate Similarity	NPD7003	Approved
0.7258	Intermediate Similarity	NPD7340	Approved
0.7234	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7041	Phase 2
0.7231	Intermediate Similarity	NPD1470	Approved
0.7222	Intermediate Similarity	NPD1651	Approved
0.7194	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1610	Phase 2
0.7183	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD3645	Discontinued
0.7177	Intermediate Similarity	NPD7157	Approved
0.7177	Intermediate Similarity	NPD6671	Approved
0.7176	Intermediate Similarity	NPD6584	Phase 3
0.7154	Intermediate Similarity	NPD1398	Phase 1
0.7154	Intermediate Similarity	NPD5283	Phase 1
0.7154	Intermediate Similarity	NPD8651	Approved
0.7153	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7330	Discontinued
0.7143	Intermediate Similarity	NPD7741	Discontinued
0.7132	Intermediate Similarity	NPD2230	Approved
0.7132	Intermediate Similarity	NPD2232	Approved
0.7132	Intermediate Similarity	NPD2233	Approved
0.7122	Intermediate Similarity	NPD7037	Approved
0.7101	Intermediate Similarity	NPD5408	Approved
0.7101	Intermediate Similarity	NPD5405	Approved
0.7101	Intermediate Similarity	NPD5404	Approved
0.7101	Intermediate Similarity	NPD5406	Approved
0.7092	Intermediate Similarity	NPD8131	Suspended
0.7087	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD4659	Approved
0.7077	Intermediate Similarity	NPD1669	Approved
0.7077	Intermediate Similarity	NPD4749	Approved
0.7063	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3657	Discovery
0.7054	Intermediate Similarity	NPD1281	Approved
0.7037	Intermediate Similarity	NPD8032	Phase 2
0.7029	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2684	Approved
0.7014	Intermediate Similarity	NPD6273	Approved
0.7009	Intermediate Similarity	NPD3028	Approved
0.7007	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2157	Approved
0.6993	Remote Similarity	NPD2421	Approved
0.6993	Remote Similarity	NPD2420	Approved
0.6992	Remote Similarity	NPD4208	Discontinued
0.6992	Remote Similarity	NPD228	Approved
0.6985	Remote Similarity	NPD3110	Approved
0.6985	Remote Similarity	NPD3109	Approved
0.6985	Remote Similarity	NPD2238	Phase 2
0.6977	Remote Similarity	NPD3143	Discontinued
0.697	Remote Similarity	NPD4103	Phase 2
0.697	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD5451	Approved
0.6966	Remote Similarity	NPD5699	Approved
0.6963	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.696	Remote Similarity	NPD1793	Approved
0.696	Remote Similarity	NPD1791	Approved
0.696	Remote Similarity	NPD5951	Approved
0.6957	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.695	Remote Similarity	NPD6674	Discontinued
0.6947	Remote Similarity	NPD6583	Phase 3
0.6947	Remote Similarity	NPD6582	Phase 2
0.6929	Remote Similarity	NPD5762	Approved
0.6929	Remote Similarity	NPD5763	Approved
0.6929	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6407	Approved
0.6912	Remote Similarity	NPD6405	Approved
0.6906	Remote Similarity	NPD4108	Discontinued
0.6905	Remote Similarity	NPD709	Approved
0.6899	Remote Similarity	NPD2667	Approved
0.6899	Remote Similarity	NPD2668	Approved
0.6891	Remote Similarity	NPD9500	Approved
0.6889	Remote Similarity	NPD7095	Approved
0.6889	Remote Similarity	NPD3027	Phase 3
0.6879	Remote Similarity	NPD4257	Approved
0.6879	Remote Similarity	NPD4256	Phase 2
0.6875	Remote Similarity	NPD1548	Phase 1
0.6875	Remote Similarity	NPD7390	Discontinued
0.687	Remote Similarity	NPD3070	Discontinued
0.6861	Remote Similarity	NPD2979	Phase 3
0.6857	Remote Similarity	NPD6100	Approved
0.6857	Remote Similarity	NPD6099	Approved
0.685	Remote Similarity	NPD405	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7636	Approved
0.6846	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1133	Approved
0.6842	Remote Similarity	NPD1134	Approved
0.6842	Remote Similarity	NPD1135	Approved
0.6842	Remote Similarity	NPD1129	Approved
0.6842	Remote Similarity	NPD1131	Approved
0.6838	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7294	Phase 1
0.6829	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD9614	Approved
0.6825	Remote Similarity	NPD9618	Approved
0.6825	Remote Similarity	NPD2629	Approved
0.6825	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD1357	Approved
0.68	Remote Similarity	NPD7843	Approved
0.6794	Remote Similarity	NPD1611	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