NPASS Compound

Structure

CID291564 OpenBabel06191716102D 43 48 0 0 1 0 0 0 0 0999 V2000 1.0286 3.1688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5178 3.5544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7926 2.3037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0541 -0.1908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2022 0.3011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0893 1.2832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0896 0.2996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4977 1.2842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6452 1.7761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3845 2.0657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2027 -1.6674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6460 -1.1760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8511 -1.4751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8289 1.3726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0065 3.0663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9401 2.7588 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4066 2.1682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0544 -1.1750 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3505 -0.1913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4980 0.3006 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6457 -0.1918 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3508 -1.1755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9404 1.7756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7932 0.3001 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4985 -1.6679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9622 2.8613 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8514 -0.4919 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7030 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7033 0.9827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8519 1.4746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5842 3.8619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9832 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7929 1.2837 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0006 -1.9664 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9206 -1.6748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4988 -2.6679 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5544 -0.4923 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5549 1.4741 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8522 2.4578 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1840 4.7600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8511 1.4751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5620 3.7594 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 4 5 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 7 1 0 0 0 0 6 23 1 0 0 0 0 7 24 1 0 0 0 0 8 9 1 0 0 0 0 9 33 1 0 0 0 0 10 17 1 0 0 0 0 10 26 1 0 0 0 0 11 18 1 0 0 0 0 11 22 1 0 0 0 0 12 25 1 0 0 0 0 13 34 1 0 0 0 0 14 17 1 0 0 0 0 14 41 1 0 0 0 0 15 17 2 0 0 0 0 15 31 1 0 0 0 0 16 2 1 1 0 0 0 16 23 1 0 0 0 0 18 35 1 1 0 0 0 19 20 1 0 0 0 0 19 22 2 0 0 0 0 20 8 1 6 0 0 0 20 21 1 0 0 0 0 21 12 1 1 0 0 0 21 24 1 0 0 0 0 22 25 1 0 0 0 0 23 33 1 6 0 0 0 24 33 1 6 0 0 0 25 36 2 0 0 0 0 26 16 1 1 0 0 0 26 42 1 0 0 0 0 27 13 1 6 0 0 0 27 28 1 0 0 0 0 27 43 1 0 0 0 0 28 29 1 0 0 0 0 28 37 1 1 0 0 0 29 30 1 0 0 0 0 29 38 1 6 0 0 0 30 32 1 0 0 0 0 30 39 1 1 0 0 0 31 40 2 0 0 0 0 31 42 1 0 0 0 0 32 41 1 6 0 0 0 32 43 1 0 0 0 0 33 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	604.32
Volume:	605.342
LogP:	2.49
LogD:	2.455
LogS:	-4.394
# Rotatable Bonds:	6
TPSA:	162.98
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.283
Synthetic Accessibility Score:	5.482
Fsp3:	0.818
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.716
MDCK Permeability:	2.7350482923793606e-05
Pgp-inhibitor:	0.825
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.966
20% Bioavailability (F20%):	0.3
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	86.0251235961914%
Volume Distribution (VD):	1.222
Pgp-substrate:	5.19614839553833%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.11
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.449
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.038
CYP3A4-inhibitor:	0.431
CYP3A4-substrate:	0.534

ADMET: Excretion

Clearance (CL):	1.73
Half-life (T1/2):	0.705

ADMET: Toxicity

hERG Blockers:	0.288
Human Hepatotoxicity (H-HT):	0.253
Drug-inuced Liver Injury (DILI):	0.415
AMES Toxicity:	0.081
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.561
Carcinogencity:	0.745
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.895

Download Data

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

Natural Product: NPC291564

Natural Product ID:	NPC291564
*Common Name:**	Withalongolide N
IUPAC Name:	(2R)-2-[(1S)-1-[(3R,8S,9S,13S,14S,17R)-3-hydroxy-13-methyl-6-oxo-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-5-methyl-4-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydropyran-6-one
Synonyms:	Withalongolide N
Standard InCHIKey:	GCUKFNAJZUUBSQ-HCGFFNIQSA-N
Standard InCHI:	InChI=1S/C33H48O10/c1-15-17(14-41-32-30(39)29(38)28(37)27(13-34)43-32)10-26(42-31(15)40)16(2)23-6-7-24-21-12-25(36)22-11-18(35)4-5-19(22)20(21)8-9-33(23,24)3/h16,18,20-21,23-24,26-30,32,34-35,37-39H,4-14H2,1-3H3/t16-,18+,20+,21+,23+,24-,26+,27+,28+,29-,30+,32+,33+/m0/s1
SMILES:	OC[C@H]1O[C@@H](OCC2=C(C)C(=O)O[C@H](C2)[C@H]([C@H]2CC[C@@H]3[C@]2(C)CC[C@H]2[C@H]3CC(=O)C3=C2CC[C@H](C3)O)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1934466
PubChem CID:	56926295
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*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
NPO14874	Physalis longifolia	Species	Solanaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22098611]
NPO14874	Physalis longifolia	Species	Solanaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[22098611]
NPO14874	Physalis longifolia	Species	Solanaceae	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	5

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT169	Cell Line	B16-F10	Mus musculus	IC50	>	10000.0	nM	PMID[511782]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	>	10000.0	nM	PMID[511782]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[511782]
NPT27	Others	Unspecified		IC50	>	10000.0	nM	PMID[511782]

☑ 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 NPC291564 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	263
0.1-0.2	1544
0.2-0.3	4892
0.3-0.4	9660
0.4-0.5	10757
0.5-0.6	6644
0.6-0.7	5932
0.7-0.8	2849
0.8-0.85	119
0.85-0.9	33
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9727	High Similarity	NPC232258
0.9554	High Similarity	NPC129434
0.9068	High Similarity	NPC245094
0.8992	High Similarity	NPC476966
0.8974	High Similarity	NPC318135
0.8919	High Similarity	NPC477073
0.8909	High Similarity	NPC477070
0.8909	High Similarity	NPC477069
0.8879	High Similarity	NPC202051
0.887	High Similarity	NPC477071
0.886	High Similarity	NPC477252
0.8843	High Similarity	NPC231240
0.8839	High Similarity	NPC233003
0.8839	High Similarity	NPC477253
0.8772	High Similarity	NPC207637
0.877	High Similarity	NPC316915
0.8761	High Similarity	NPC477074
0.8761	High Similarity	NPC251309
0.876	High Similarity	NPC173347
0.8718	High Similarity	NPC170084
0.8718	High Similarity	NPC476204
0.8678	High Similarity	NPC471407
0.8661	High Similarity	NPC27551
0.8661	High Similarity	NPC129340
0.8661	High Similarity	NPC114961
0.8649	High Similarity	NPC195708
0.8632	High Similarity	NPC470312
0.8621	High Similarity	NPC473828
0.8621	High Similarity	NPC473617
0.8571	High Similarity	NPC265655
0.8559	High Similarity	NPC187950
0.8559	High Similarity	NPC278163
0.8547	High Similarity	NPC475834
0.8547	High Similarity	NPC474179
0.8545	High Similarity	NPC223741
0.8537	High Similarity	NPC471855
0.8522	High Similarity	NPC220293
0.8522	High Similarity	NPC473882
0.8482	Intermediate Similarity	NPC295389
0.8468	Intermediate Similarity	NPC162033
0.8462	Intermediate Similarity	NPC475913
0.8462	Intermediate Similarity	NPC45475
0.8455	Intermediate Similarity	NPC213634
0.8443	Intermediate Similarity	NPC311534
0.8435	Intermediate Similarity	NPC73455
0.8435	Intermediate Similarity	NPC260665
0.8435	Intermediate Similarity	NPC200944
0.8421	Intermediate Similarity	NPC263827
0.8421	Intermediate Similarity	NPC285410
0.8421	Intermediate Similarity	NPC250481
0.8421	Intermediate Similarity	NPC292196
0.8417	Intermediate Similarity	NPC41129
0.8407	Intermediate Similarity	NPC118225
0.8407	Intermediate Similarity	NPC246205
0.8374	Intermediate Similarity	NPC473593
0.8362	Intermediate Similarity	NPC74727
0.8362	Intermediate Similarity	NPC475163
0.8362	Intermediate Similarity	NPC165439
0.8361	Intermediate Similarity	NPC240070
0.8361	Intermediate Similarity	NPC329784
0.8348	Intermediate Similarity	NPC471967
0.8348	Intermediate Similarity	NPC210420
0.8348	Intermediate Similarity	NPC474265
0.8348	Intermediate Similarity	NPC236217
0.8347	Intermediate Similarity	NPC6615
0.8347	Intermediate Similarity	NPC7850
0.8333	Intermediate Similarity	NPC52241
0.8333	Intermediate Similarity	NPC28532
0.8333	Intermediate Similarity	NPC83005
0.8333	Intermediate Similarity	NPC475317
0.8333	Intermediate Similarity	NPC154856
0.8319	Intermediate Similarity	NPC325054
0.8319	Intermediate Similarity	NPC129393
0.8319	Intermediate Similarity	NPC285576
0.8319	Intermediate Similarity	NPC476127
0.8319	Intermediate Similarity	NPC48692
0.8319	Intermediate Similarity	NPC471406
0.8319	Intermediate Similarity	NPC476150
0.8305	Intermediate Similarity	NPC239293
0.8281	Intermediate Similarity	NPC79250
0.8281	Intermediate Similarity	NPC290746
0.8279	Intermediate Similarity	NPC47113
0.8279	Intermediate Similarity	NPC174367
0.8276	Intermediate Similarity	NPC311592
0.8276	Intermediate Similarity	NPC75167
0.8264	Intermediate Similarity	NPC27363
0.8261	Intermediate Similarity	NPC191763
0.8261	Intermediate Similarity	NPC190837
0.825	Intermediate Similarity	NPC47567
0.825	Intermediate Similarity	NPC258789
0.825	Intermediate Similarity	NPC241310
0.825	Intermediate Similarity	NPC169727
0.825	Intermediate Similarity	NPC194310
0.825	Intermediate Similarity	NPC258815
0.825	Intermediate Similarity	NPC412
0.825	Intermediate Similarity	NPC131841
0.8246	Intermediate Similarity	NPC137917
0.8235	Intermediate Similarity	NPC190939
0.8235	Intermediate Similarity	NPC122971
0.8235	Intermediate Similarity	NPC258592
0.8235	Intermediate Similarity	NPC197003
0.8235	Intermediate Similarity	NPC178548
0.823	Intermediate Similarity	NPC293512
0.8226	Intermediate Similarity	NPC140092
0.8226	Intermediate Similarity	NPC188234
0.8226	Intermediate Similarity	NPC232785
0.8226	Intermediate Similarity	NPC276838
0.8226	Intermediate Similarity	NPC329986
0.8226	Intermediate Similarity	NPC125077
0.822	Intermediate Similarity	NPC473405
0.822	Intermediate Similarity	NPC203862
0.822	Intermediate Similarity	NPC474483
0.8211	Intermediate Similarity	NPC42399
0.8211	Intermediate Similarity	NPC470516
0.8205	Intermediate Similarity	NPC181145
0.8205	Intermediate Similarity	NPC474557
0.8205	Intermediate Similarity	NPC116024
0.8197	Intermediate Similarity	NPC3381
0.8197	Intermediate Similarity	NPC30188
0.8197	Intermediate Similarity	NPC130229
0.8197	Intermediate Similarity	NPC177820
0.819	Intermediate Similarity	NPC195132
0.819	Intermediate Similarity	NPC64106
0.819	Intermediate Similarity	NPC46388
0.819	Intermediate Similarity	NPC212968
0.819	Intermediate Similarity	NPC256798
0.819	Intermediate Similarity	NPC37739
0.819	Intermediate Similarity	NPC65590
0.819	Intermediate Similarity	NPC128925
0.819	Intermediate Similarity	NPC130427
0.819	Intermediate Similarity	NPC161434
0.819	Intermediate Similarity	NPC116794
0.819	Intermediate Similarity	NPC125923
0.8189	Intermediate Similarity	NPC158350
0.8182	Intermediate Similarity	NPC23786
0.8182	Intermediate Similarity	NPC156789
0.8182	Intermediate Similarity	NPC470265
0.8175	Intermediate Similarity	NPC477709
0.8175	Intermediate Similarity	NPC104585
0.8175	Intermediate Similarity	NPC157817
0.8175	Intermediate Similarity	NPC225385
0.8175	Intermediate Similarity	NPC298783
0.8175	Intermediate Similarity	NPC142756
0.8175	Intermediate Similarity	NPC476221
0.8174	Intermediate Similarity	NPC90630
0.8174	Intermediate Similarity	NPC274507
0.8174	Intermediate Similarity	NPC269095
0.8174	Intermediate Similarity	NPC220984
0.8174	Intermediate Similarity	NPC475243
0.8174	Intermediate Similarity	NPC78046
0.8167	Intermediate Similarity	NPC251226
0.8167	Intermediate Similarity	NPC281840
0.8167	Intermediate Similarity	NPC476849
0.8167	Intermediate Similarity	NPC107607
0.8167	Intermediate Similarity	NPC308459
0.816	Intermediate Similarity	NPC16569
0.816	Intermediate Similarity	NPC253456
0.816	Intermediate Similarity	NPC159338
0.8158	Intermediate Similarity	NPC272576
0.8158	Intermediate Similarity	NPC88744
0.8158	Intermediate Similarity	NPC392
0.8158	Intermediate Similarity	NPC219900
0.8158	Intermediate Similarity	NPC177524
0.8151	Intermediate Similarity	NPC471548
0.8151	Intermediate Similarity	NPC86020
0.8151	Intermediate Similarity	NPC234522
0.8151	Intermediate Similarity	NPC218093
0.8151	Intermediate Similarity	NPC276758
0.8151	Intermediate Similarity	NPC475632
0.8151	Intermediate Similarity	NPC18233
0.8145	Intermediate Similarity	NPC45606
0.8145	Intermediate Similarity	NPC473620
0.8145	Intermediate Similarity	NPC220838
0.8142	Intermediate Similarity	NPC210178
0.8136	Intermediate Similarity	NPC244127
0.8136	Intermediate Similarity	NPC279638
0.813	Intermediate Similarity	NPC469750
0.813	Intermediate Similarity	NPC250556
0.812	Intermediate Similarity	NPC474410
0.812	Intermediate Similarity	NPC293658
0.812	Intermediate Similarity	NPC138334
0.812	Intermediate Similarity	NPC269315
0.812	Intermediate Similarity	NPC189884
0.812	Intermediate Similarity	NPC271138
0.812	Intermediate Similarity	NPC204458
0.812	Intermediate Similarity	NPC293038
0.812	Intermediate Similarity	NPC62696
0.812	Intermediate Similarity	NPC47063
0.812	Intermediate Similarity	NPC477944
0.812	Intermediate Similarity	NPC473159
0.8115	Intermediate Similarity	NPC160084
0.8115	Intermediate Similarity	NPC256983
0.8103	Intermediate Similarity	NPC473481
0.8103	Intermediate Similarity	NPC274833
0.8103	Intermediate Similarity	NPC108748
0.8103	Intermediate Similarity	NPC297208
0.8103	Intermediate Similarity	NPC30397
0.8103	Intermediate Similarity	NPC211798
0.8103	Intermediate Similarity	NPC235841
0.8099	Intermediate Similarity	NPC4021

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 NPC291564 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	252
0.1-0.2	1855
0.2-0.3	3853
0.3-0.4	2094
0.4-0.5	580
0.5-0.6	263
0.6-0.7	208
0.7-0.8	42
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD8132	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD6686	Approved
0.813	Intermediate Similarity	NPD7507	Approved
0.812	Intermediate Similarity	NPD8133	Approved
0.8099	Intermediate Similarity	NPD8033	Approved
0.807	Intermediate Similarity	NPD6412	Phase 2
0.8017	Intermediate Similarity	NPD8377	Approved
0.8017	Intermediate Similarity	NPD8294	Approved
0.7951	Intermediate Similarity	NPD8379	Approved
0.7951	Intermediate Similarity	NPD8296	Approved
0.7951	Intermediate Similarity	NPD8380	Approved
0.7951	Intermediate Similarity	NPD8378	Approved
0.7951	Intermediate Similarity	NPD8335	Approved
0.7951	Intermediate Similarity	NPD7503	Approved
0.7937	Intermediate Similarity	NPD7319	Approved
0.7917	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7851	Intermediate Similarity	NPD7327	Approved
0.7851	Intermediate Similarity	NPD7328	Approved
0.7823	Intermediate Similarity	NPD8328	Phase 3
0.7787	Intermediate Similarity	NPD7516	Approved
0.7769	Intermediate Similarity	NPD7115	Discovery
0.7661	Intermediate Similarity	NPD8513	Phase 3
0.752	Intermediate Similarity	NPD8517	Approved
0.752	Intermediate Similarity	NPD8516	Approved
0.752	Intermediate Similarity	NPD8515	Approved
0.7479	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7736	Approved
0.7417	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD8293	Discontinued
0.7355	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD7638	Approved
0.7288	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7640	Approved
0.7241	Intermediate Similarity	NPD7639	Approved
0.7188	Intermediate Similarity	NPD6370	Approved
0.7168	Intermediate Similarity	NPD6399	Phase 3
0.7167	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD8297	Approved
0.7154	Intermediate Similarity	NPD6882	Approved
0.7119	Intermediate Similarity	NPD7632	Discontinued
0.7077	Intermediate Similarity	NPD7492	Approved
0.7069	Intermediate Similarity	NPD7902	Approved
0.7063	Intermediate Similarity	NPD6009	Approved
0.7049	Intermediate Similarity	NPD6372	Approved
0.7049	Intermediate Similarity	NPD6373	Approved
0.7031	Intermediate Similarity	NPD6319	Approved
0.7031	Intermediate Similarity	NPD6054	Approved
0.7031	Intermediate Similarity	NPD6059	Approved
0.7023	Intermediate Similarity	NPD6616	Approved
0.7016	Intermediate Similarity	NPD6053	Discontinued
0.6991	Remote Similarity	NPD6698	Approved
0.6991	Remote Similarity	NPD46	Approved
0.697	Remote Similarity	NPD7078	Approved
0.696	Remote Similarity	NPD4632	Approved
0.6957	Remote Similarity	NPD7748	Approved
0.6942	Remote Similarity	NPD7128	Approved
0.6942	Remote Similarity	NPD6675	Approved
0.6942	Remote Similarity	NPD6402	Approved
0.6942	Remote Similarity	NPD5739	Approved
0.6935	Remote Similarity	NPD6649	Approved
0.6935	Remote Similarity	NPD6650	Approved
0.687	Remote Similarity	NPD6067	Discontinued
0.6864	Remote Similarity	NPD4225	Approved
0.6846	Remote Similarity	NPD6015	Approved
0.6846	Remote Similarity	NPD6016	Approved
0.6829	Remote Similarity	NPD7320	Approved
0.6829	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6899	Approved
0.6829	Remote Similarity	NPD6881	Approved
0.681	Remote Similarity	NPD7900	Approved
0.681	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6008	Approved
0.68	Remote Similarity	NPD8130	Phase 1
0.6794	Remote Similarity	NPD5988	Approved
0.6783	Remote Similarity	NPD7515	Phase 2
0.6783	Remote Similarity	NPD8034	Phase 2
0.6783	Remote Similarity	NPD8035	Phase 2
0.678	Remote Similarity	NPD6084	Phase 2
0.678	Remote Similarity	NPD6083	Phase 2
0.6765	Remote Similarity	NPD7260	Phase 2
0.6752	Remote Similarity	NPD5695	Phase 3
0.6748	Remote Similarity	NPD5701	Approved
0.6748	Remote Similarity	NPD5697	Approved
0.6724	Remote Similarity	NPD8171	Discontinued
0.6723	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7290	Approved
0.672	Remote Similarity	NPD6883	Approved
0.672	Remote Similarity	NPD6371	Approved
0.672	Remote Similarity	NPD7102	Approved
0.6716	Remote Similarity	NPD8074	Phase 3
0.6715	Remote Similarity	NPD6845	Suspended
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.664	Remote Similarity	NPD6013	Approved
0.664	Remote Similarity	NPD6012	Approved
0.664	Remote Similarity	NPD6014	Approved
0.6637	Remote Similarity	NPD3618	Phase 1
0.6617	Remote Similarity	NPD7604	Phase 2
0.6613	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5328	Approved
0.6607	Remote Similarity	NPD4786	Approved
0.6591	Remote Similarity	NPD5983	Phase 2
0.6583	Remote Similarity	NPD5696	Approved
0.656	Remote Similarity	NPD6011	Approved
0.6544	Remote Similarity	NPD6033	Approved
0.6535	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5737	Approved
0.6522	Remote Similarity	NPD6672	Approved
0.6522	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD6336	Discontinued
0.65	Remote Similarity	NPD4755	Approved
0.6496	Remote Similarity	NPD5284	Approved
0.6496	Remote Similarity	NPD6079	Approved
0.6496	Remote Similarity	NPD5281	Approved
0.6491	Remote Similarity	NPD6409	Approved
0.6491	Remote Similarity	NPD5330	Approved
0.6491	Remote Similarity	NPD6684	Approved
0.6491	Remote Similarity	NPD7334	Approved
0.6491	Remote Similarity	NPD7521	Approved
0.6491	Remote Similarity	NPD7146	Approved
0.6463	Remote Similarity	NPD7625	Phase 1
0.6462	Remote Similarity	NPD6940	Discontinued
0.646	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD4634	Approved
0.6441	Remote Similarity	NPD4202	Approved
0.6429	Remote Similarity	NPD3667	Approved
0.6423	Remote Similarity	NPD5211	Phase 2
0.6423	Remote Similarity	NPD8336	Approved
0.6423	Remote Similarity	NPD8337	Approved
0.6417	Remote Similarity	NPD4697	Phase 3
0.641	Remote Similarity	NPD7838	Discovery
0.6404	Remote Similarity	NPD1694	Approved
0.6404	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD4700	Approved
0.6393	Remote Similarity	NPD4696	Approved
0.6393	Remote Similarity	NPD5285	Approved
0.6393	Remote Similarity	NPD5286	Approved
0.6379	Remote Similarity	NPD6903	Approved
0.6356	Remote Similarity	NPD6411	Approved
0.6356	Remote Similarity	NPD5693	Phase 1
0.6348	Remote Similarity	NPD5279	Phase 3
0.6343	Remote Similarity	NPD6921	Approved
0.6341	Remote Similarity	NPD5344	Discontinued
0.6336	Remote Similarity	NPD6274	Approved
0.6333	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD4753	Phase 2
0.6325	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.632	Remote Similarity	NPD5141	Approved
0.6316	Remote Similarity	NPD3665	Phase 1
0.6316	Remote Similarity	NPD3133	Approved
0.6316	Remote Similarity	NPD7101	Approved
0.6316	Remote Similarity	NPD7100	Approved
0.6316	Remote Similarity	NPD3666	Approved
0.6303	Remote Similarity	NPD5779	Approved
0.6303	Remote Similarity	NPD5778	Approved
0.6296	Remote Similarity	NPD8080	Discontinued
0.629	Remote Similarity	NPD5225	Approved
0.629	Remote Similarity	NPD5226	Approved
0.629	Remote Similarity	NPD4633	Approved
0.629	Remote Similarity	NPD5224	Approved
0.6281	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD5222	Approved
0.6281	Remote Similarity	NPD5221	Approved
0.6271	Remote Similarity	NPD5785	Approved
0.627	Remote Similarity	NPD4767	Approved
0.627	Remote Similarity	NPD4768	Approved
0.6258	Remote Similarity	NPD7799	Discontinued
0.625	Remote Similarity	NPD7829	Approved
0.625	Remote Similarity	NPD7830	Approved
0.625	Remote Similarity	NPD7642	Approved
0.6241	Remote Similarity	NPD6335	Approved
0.6241	Remote Similarity	NPD8449	Approved
0.6241	Remote Similarity	NPD8338	Approved
0.624	Remote Similarity	NPD5174	Approved
0.624	Remote Similarity	NPD5175	Approved
0.623	Remote Similarity	NPD5173	Approved
0.6222	Remote Similarity	NPD6908	Approved
0.6222	Remote Similarity	NPD6909	Approved
0.6218	Remote Similarity	NPD6050	Approved
0.6218	Remote Similarity	NPD7983	Approved
0.6218	Remote Similarity	NPD7637	Suspended
0.6216	Remote Similarity	NPD6114	Approved
0.6216	Remote Similarity	NPD6697	Approved
0.6216	Remote Similarity	NPD6118	Approved
0.6216	Remote Similarity	NPD6115	Approved
0.6214	Remote Similarity	NPD5956	Approved
0.6212	Remote Similarity	NPD6868	Approved
0.621	Remote Similarity	NPD5223	Approved
0.6198	Remote Similarity	NPD5210	Approved
0.6198	Remote Similarity	NPD4629	Approved
0.6197	Remote Similarity	NPD8450	Suspended
0.6186	Remote Similarity	NPD6673	Approved
0.6186	Remote Similarity	NPD6101	Approved
0.6186	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6904	Approved
0.6186	Remote Similarity	NPD6080	Approved
0.6172	Remote Similarity	NPD4730	Approved
0.6172	Remote Similarity	NPD4729	Approved
0.6165	Remote Similarity	NPD6317	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