NPASS Compound

Structure

NPC471333 OpenBabel07101718192D 47 50 0 0 1 0 0 0 0 0999 V2000 -0.0973 4.5472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6465 3.9392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8161 1.2424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9839 2.6836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6680 1.8019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2284 1.2234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3212 -0.6749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -1.3890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4679 -4.2745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6358 -3.7941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5591 -0.2336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4586 0.7220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3567 1.1127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6048 2.7584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3454 2.9016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1518 1.2424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1518 0.2815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3068 0.9695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3285 0.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3751 -0.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0319 -2.3811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5917 -1.5527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6964 3.7960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9839 1.7228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2812 1.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3197 -0.1989 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6642 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2009 -0.6749 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1606 0.4804 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9875 -2.4816 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9472 0.1612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8321 0.4804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6642 -0.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2610 -0.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4679 -3.3137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6813 0.1572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7078 0.2183 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8321 -1.4413 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0269 -2.3301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5605 -0.5785 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8321 1.4413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8321 -1.4413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4287 -3.3137 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3783 -1.6038 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0384 0.8712 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 25 1 0 0 0 0 7 35 1 0 0 0 0 8 35 1 0 0 0 0 9 36 1 0 0 0 0 10 36 1 0 0 0 0 11 37 1 0 0 0 0 12 37 1 0 0 0 0 13 38 1 0 0 0 0 14 15 1 0 0 0 0 14 18 1 0 0 0 0 15 23 2 0 0 0 0 16 17 1 0 0 0 0 16 24 2 0 0 0 0 17 26 1 0 0 0 0 18 38 1 0 0 0 0 19 27 1 0 0 0 0 20 26 1 0 0 0 0 21 30 1 0 0 0 0 21 39 1 0 0 0 0 22 41 1 0 0 0 0 25 31 1 0 0 0 0 26 38 1 1 0 0 0 27 32 1 0 0 0 0 27 33 2 0 0 0 0 28 22 1 6 0 0 0 28 35 1 0 0 0 0 28 37 1 0 0 0 0 29 19 1 1 0 0 0 29 35 1 0 0 0 0 29 47 1 0 0 0 0 30 36 1 6 0 0 0 30 46 1 0 0 0 0 31 42 2 0 0 0 0 32 40 1 0 0 0 0 32 43 2 0 0 0 0 33 39 1 0 0 0 0 33 46 1 0 0 0 0 34 39 1 0 0 0 0 34 40 1 0 0 0 0 34 44 2 0 0 0 0 36 45 1 0 0 0 0 37 47 1 0 0 0 0 38 40 1 6 0 0 0 39 20 1 1 0 0 0 40 31 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	654.45
Volume:	711.883
LogP:	7.796
LogD:	5.329
LogS:	-5.369
# Rotatable Bonds:	11
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.176
Synthetic Accessibility Score:	6.915
Fsp3:	0.775
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.338
MDCK Permeability:	1.3821962056681514e-05
Pgp-inhibitor:	0.036
Pgp-substrate:	0.698
Human Intestinal Absorption (HIA):	0.108
20% Bioavailability (F20%):	0.958
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.931
Plasma Protein Binding (PPB):	87.15055084228516%
Volume Distribution (VD):	1.593
Pgp-substrate:	6.680893898010254%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.871
CYP2C9-inhibitor:	0.109
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.013
CYP3A4-inhibitor:	0.817
CYP3A4-substrate:	0.921

ADMET: Excretion

Clearance (CL):	10.657
Half-life (T1/2):	0.013

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.939
Drug-inuced Liver Injury (DILI):	0.809
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.861
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.332
Carcinogencity:	0.571
Eye Corrosion:	0.004
Eye Irritation:	0.022
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC471333

Natural Product ID:	NPC471333
*Common Name:**	JTAANBDQXPMQPN-XMSARYDJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JTAANBDQXPMQPN-XMSARYDJSA-N
Standard InCHI:	InChI=1S/C40H62O7/c1-23(2)15-14-18-38(13)26(17-16-24(3)4)20-39-21-30(36(9,10)45)46-33(39)27(32(43)40(38,34(39)44)31(42)25(5)6)19-29-35(7,8)28(22-41)37(11,12)47-29/h15-16,25-26,28-30,41,45H,14,17-22H2,1-13H3/t26-,28+,29+,30-,38+,39-,40-/m0/s1
SMILES:	OC[C@H]1C(C)(C)O[C@@H](C1(C)C)CC1=C2O[C@@H](C[C@]32C[C@@H]([C@@]([C@@](C1=O)(C3=O)C(=O)C(C)C)(C)CCC=C(C)C)CC=C(C)C)C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419286
PubChem CID:	73350740
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene 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
NPO33449	hypericum cohaerens	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23957453]

☑ 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	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	7400.0	nM	PMID[547512]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	9300.0	nM	PMID[547512]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	5600.0	nM	PMID[547512]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	9500.0	nM	PMID[547512]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	8800.0	nM	PMID[547512]

☑ 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 NPC471333 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	209
0.1-0.2	1167
0.2-0.3	4531
0.3-0.4	8551
0.4-0.5	12964
0.5-0.6	7538
0.6-0.7	6581
0.7-0.8	1099
0.8-0.85	29
0.85-0.9	15
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471332
0.9381	High Similarity	NPC99657
0.9381	High Similarity	NPC203388
0.9381	High Similarity	NPC471330
0.9381	High Similarity	NPC471331
0.9381	High Similarity	NPC472687
0.9278	High Similarity	NPC27105
0.9082	High Similarity	NPC472731
0.9082	High Similarity	NPC472732
0.898	High Similarity	NPC472733
0.898	High Similarity	NPC472734
0.89	High Similarity	NPC472727
0.89	High Similarity	NPC472728
0.88	High Similarity	NPC153776
0.88	High Similarity	NPC472730
0.88	High Similarity	NPC177680
0.88	High Similarity	NPC472729
0.8586	High Similarity	NPC114162
0.8586	High Similarity	NPC469819
0.8416	Intermediate Similarity	NPC472675
0.8416	Intermediate Similarity	NPC21681
0.8364	Intermediate Similarity	NPC247069
0.8351	Intermediate Similarity	NPC38885
0.8288	Intermediate Similarity	NPC207217
0.8241	Intermediate Similarity	NPC470257
0.8235	Intermediate Similarity	NPC8803
0.8235	Intermediate Similarity	NPC93271
0.8235	Intermediate Similarity	NPC135576
0.8095	Intermediate Similarity	NPC181645
0.8095	Intermediate Similarity	NPC101067
0.8095	Intermediate Similarity	NPC476134
0.8081	Intermediate Similarity	NPC476708
0.8056	Intermediate Similarity	NPC58370
0.8056	Intermediate Similarity	NPC43285
0.8037	Intermediate Similarity	NPC255309
0.8036	Intermediate Similarity	NPC117712
0.8019	Intermediate Similarity	NPC476235
0.8019	Intermediate Similarity	NPC476126
0.8018	Intermediate Similarity	NPC207251
0.8	Intermediate Similarity	NPC5284
0.8	Intermediate Similarity	NPC478051
0.7982	Intermediate Similarity	NPC473288
0.7982	Intermediate Similarity	NPC106644
0.7981	Intermediate Similarity	NPC239895
0.7963	Intermediate Similarity	NPC102352
0.7963	Intermediate Similarity	NPC96377
0.7928	Intermediate Similarity	NPC324683
0.7925	Intermediate Similarity	NPC477870
0.7925	Intermediate Similarity	NPC476213
0.7925	Intermediate Similarity	NPC477871
0.7925	Intermediate Similarity	NPC476246
0.7925	Intermediate Similarity	NPC9878
0.7909	Intermediate Similarity	NPC87335
0.79	Intermediate Similarity	NPC476706
0.79	Intermediate Similarity	NPC476707
0.7895	Intermediate Similarity	NPC97908
0.7895	Intermediate Similarity	NPC122033
0.7895	Intermediate Similarity	NPC287343
0.7895	Intermediate Similarity	NPC474654
0.7895	Intermediate Similarity	NPC470854
0.789	Intermediate Similarity	NPC144854
0.789	Intermediate Similarity	NPC3316
0.789	Intermediate Similarity	NPC59530
0.7876	Intermediate Similarity	NPC326542
0.787	Intermediate Similarity	NPC471293
0.787	Intermediate Similarity	NPC13385
0.787	Intermediate Similarity	NPC146731
0.787	Intermediate Similarity	NPC296950
0.7864	Intermediate Similarity	NPC196227
0.7857	Intermediate Similarity	NPC269530
0.785	Intermediate Similarity	NPC473163
0.785	Intermediate Similarity	NPC478176
0.7838	Intermediate Similarity	NPC5103
0.783	Intermediate Similarity	NPC167974
0.7826	Intermediate Similarity	NPC297179
0.7826	Intermediate Similarity	NPC17772
0.7818	Intermediate Similarity	NPC192813
0.7818	Intermediate Similarity	NPC277017
0.7818	Intermediate Similarity	NPC154608
0.781	Intermediate Similarity	NPC124246
0.781	Intermediate Similarity	NPC473574
0.781	Intermediate Similarity	NPC20078
0.7807	Intermediate Similarity	NPC328374
0.7807	Intermediate Similarity	NPC96312
0.7807	Intermediate Similarity	NPC40632
0.7807	Intermediate Similarity	NPC251236
0.7798	Intermediate Similarity	NPC63023
0.7798	Intermediate Similarity	NPC95243
0.7797	Intermediate Similarity	NPC141196
0.7797	Intermediate Similarity	NPC238005
0.7797	Intermediate Similarity	NPC1980
0.7788	Intermediate Similarity	NPC469454
0.7788	Intermediate Similarity	NPC49451
0.7788	Intermediate Similarity	NPC473170
0.7788	Intermediate Similarity	NPC469496
0.7788	Intermediate Similarity	NPC198539
0.7788	Intermediate Similarity	NPC469463
0.7788	Intermediate Similarity	NPC52634
0.7778	Intermediate Similarity	NPC117185
0.7778	Intermediate Similarity	NPC471005
0.7768	Intermediate Similarity	NPC471243
0.7768	Intermediate Similarity	NPC474229
0.7767	Intermediate Similarity	NPC61275
0.776	Intermediate Similarity	NPC144257
0.7759	Intermediate Similarity	NPC470777
0.7748	Intermediate Similarity	NPC246205
0.7745	Intermediate Similarity	NPC469464
0.7732	Intermediate Similarity	NPC44963
0.7732	Intermediate Similarity	NPC472684
0.7727	Intermediate Similarity	NPC473165
0.7719	Intermediate Similarity	NPC473798
0.7712	Intermediate Similarity	NPC287236
0.7706	Intermediate Similarity	NPC121566
0.7706	Intermediate Similarity	NPC470104
0.7706	Intermediate Similarity	NPC258532
0.7706	Intermediate Similarity	NPC100955
0.7699	Intermediate Similarity	NPC152117
0.7699	Intermediate Similarity	NPC472002
0.7699	Intermediate Similarity	NPC234042
0.7699	Intermediate Similarity	NPC474516
0.7692	Intermediate Similarity	NPC174051
0.7692	Intermediate Similarity	NPC473172
0.7692	Intermediate Similarity	NPC477241
0.7692	Intermediate Similarity	NPC103527
0.7692	Intermediate Similarity	NPC67831
0.7685	Intermediate Similarity	NPC473928
0.7679	Intermediate Similarity	NPC235014
0.7679	Intermediate Similarity	NPC239097
0.7679	Intermediate Similarity	NPC210005
0.7679	Intermediate Similarity	NPC474567
0.7672	Intermediate Similarity	NPC204552
0.7672	Intermediate Similarity	NPC188667
0.767	Intermediate Similarity	NPC476705
0.767	Intermediate Similarity	NPC146852
0.767	Intermediate Similarity	NPC116726
0.767	Intermediate Similarity	NPC475441
0.7667	Intermediate Similarity	NPC174367
0.7667	Intermediate Similarity	NPC93368
0.7667	Intermediate Similarity	NPC47113
0.7667	Intermediate Similarity	NPC198714
0.7664	Intermediate Similarity	NPC46761
0.7664	Intermediate Similarity	NPC54705
0.7664	Intermediate Similarity	NPC474720
0.7658	Intermediate Similarity	NPC151393
0.7652	Intermediate Similarity	NPC134869
0.7652	Intermediate Similarity	NPC16081
0.7652	Intermediate Similarity	NPC235539
0.7652	Intermediate Similarity	NPC152199
0.7652	Intermediate Similarity	NPC173686
0.7647	Intermediate Similarity	NPC265557
0.7647	Intermediate Similarity	NPC18945
0.7647	Intermediate Similarity	NPC105926
0.7647	Intermediate Similarity	NPC471222
0.7647	Intermediate Similarity	NPC91693
0.7642	Intermediate Similarity	NPC477268
0.7642	Intermediate Similarity	NPC273269
0.7642	Intermediate Similarity	NPC472689
0.7642	Intermediate Similarity	NPC472690
0.7642	Intermediate Similarity	NPC477267
0.7636	Intermediate Similarity	NPC210178
0.7636	Intermediate Similarity	NPC470587
0.7636	Intermediate Similarity	NPC472655
0.7632	Intermediate Similarity	NPC7921
0.7632	Intermediate Similarity	NPC255017
0.7632	Intermediate Similarity	NPC208998
0.7632	Intermediate Similarity	NPC317210
0.7632	Intermediate Similarity	NPC194273
0.7632	Intermediate Similarity	NPC326264
0.7629	Intermediate Similarity	NPC472948
0.7627	Intermediate Similarity	NPC42675
0.7627	Intermediate Similarity	NPC477046
0.7627	Intermediate Similarity	NPC472000
0.7627	Intermediate Similarity	NPC471999
0.7627	Intermediate Similarity	NPC102822
0.7624	Intermediate Similarity	NPC474174
0.7624	Intermediate Similarity	NPC251808
0.7619	Intermediate Similarity	NPC316215
0.7619	Intermediate Similarity	NPC108141
0.7615	Intermediate Similarity	NPC474207
0.7615	Intermediate Similarity	NPC475321
0.7615	Intermediate Similarity	NPC474165
0.7615	Intermediate Similarity	NPC474330
0.7615	Intermediate Similarity	NPC474775
0.7615	Intermediate Similarity	NPC69171
0.7611	Intermediate Similarity	NPC171888
0.7611	Intermediate Similarity	NPC146945
0.7611	Intermediate Similarity	NPC317107
0.7611	Intermediate Similarity	NPC179798
0.7611	Intermediate Similarity	NPC38159
0.7611	Intermediate Similarity	NPC43775
0.7611	Intermediate Similarity	NPC201992
0.7611	Intermediate Similarity	NPC188738
0.7611	Intermediate Similarity	NPC304180
0.7596	Intermediate Similarity	NPC474807
0.7593	Intermediate Similarity	NPC475867
0.7593	Intermediate Similarity	NPC270155
0.7593	Intermediate Similarity	NPC471401
0.7593	Intermediate Similarity	NPC472753
0.7593	Intermediate Similarity	NPC97435
0.7589	Intermediate Similarity	NPC304495

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 NPC471333 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1586
0.2-0.3	4004
0.3-0.4	2256
0.4-0.5	665
0.5-0.6	235
0.6-0.7	199
0.7-0.8	32
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7864	Intermediate Similarity	NPD5282	Discontinued
0.7542	Intermediate Similarity	NPD6054	Approved
0.7542	Intermediate Similarity	NPD6059	Approved
0.7417	Intermediate Similarity	NPD6370	Approved
0.7411	Intermediate Similarity	NPD6412	Phase 2
0.7368	Intermediate Similarity	NPD4634	Approved
0.7333	Intermediate Similarity	NPD6015	Approved
0.7333	Intermediate Similarity	NPD6016	Approved
0.7317	Intermediate Similarity	NPD8293	Discontinued
0.7295	Intermediate Similarity	NPD7492	Approved
0.7273	Intermediate Similarity	NPD5988	Approved
0.7258	Intermediate Similarity	NPD7736	Approved
0.725	Intermediate Similarity	NPD6319	Approved
0.7241	Intermediate Similarity	NPD8297	Approved
0.7236	Intermediate Similarity	NPD6616	Approved
0.7213	Intermediate Similarity	NPD8328	Phase 3
0.7193	Intermediate Similarity	NPD7320	Approved
0.7177	Intermediate Similarity	NPD7078	Approved
0.7168	Intermediate Similarity	NPD5739	Approved
0.7168	Intermediate Similarity	NPD6008	Approved
0.7168	Intermediate Similarity	NPD6675	Approved
0.7168	Intermediate Similarity	NPD6402	Approved
0.7168	Intermediate Similarity	NPD7128	Approved
0.7156	Intermediate Similarity	NPD4755	Approved
0.7143	Intermediate Similarity	NPD5328	Approved
0.7143	Intermediate Similarity	NPD7115	Discovery
0.713	Intermediate Similarity	NPD6373	Approved
0.713	Intermediate Similarity	NPD6372	Approved
0.713	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6399	Phase 3
0.7094	Intermediate Similarity	NPD6053	Discontinued
0.7091	Intermediate Similarity	NPD4225	Approved
0.7043	Intermediate Similarity	NPD6881	Approved
0.7043	Intermediate Similarity	NPD6899	Approved
0.7034	Intermediate Similarity	NPD4632	Approved
0.7027	Intermediate Similarity	NPD5285	Approved
0.7027	Intermediate Similarity	NPD4700	Approved
0.7027	Intermediate Similarity	NPD5286	Approved
0.7027	Intermediate Similarity	NPD4696	Approved
0.7019	Intermediate Similarity	NPD3618	Phase 1
0.7009	Intermediate Similarity	NPD6411	Approved
0.7009	Intermediate Similarity	NPD6649	Approved
0.7009	Intermediate Similarity	NPD6650	Approved
0.7009	Intermediate Similarity	NPD8130	Phase 1
0.7009	Intermediate Similarity	NPD6079	Approved
0.7	Intermediate Similarity	NPD7902	Approved
0.7	Intermediate Similarity	NPD6083	Phase 2
0.7	Intermediate Similarity	NPD6084	Phase 2
0.699	Remote Similarity	NPD3133	Approved
0.699	Remote Similarity	NPD3666	Approved
0.699	Remote Similarity	NPD4786	Approved
0.699	Remote Similarity	NPD3665	Phase 1
0.6984	Remote Similarity	NPD6033	Approved
0.6981	Remote Similarity	NPD4753	Phase 2
0.6961	Remote Similarity	NPD3667	Approved
0.6957	Remote Similarity	NPD5701	Approved
0.6957	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5697	Approved
0.6944	Remote Similarity	NPD5778	Approved
0.6944	Remote Similarity	NPD5779	Approved
0.6923	Remote Similarity	NPD7102	Approved
0.6923	Remote Similarity	NPD6883	Approved
0.6923	Remote Similarity	NPD6371	Approved
0.6923	Remote Similarity	NPD7290	Approved
0.6909	Remote Similarity	NPD4697	Phase 3
0.6903	Remote Similarity	NPD5225	Approved
0.6903	Remote Similarity	NPD4633	Approved
0.6903	Remote Similarity	NPD5211	Phase 2
0.6903	Remote Similarity	NPD5224	Approved
0.6903	Remote Similarity	NPD5226	Approved
0.6897	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6686	Approved
0.6881	Remote Similarity	NPD7748	Approved
0.6864	Remote Similarity	NPD6847	Approved
0.6864	Remote Similarity	NPD6617	Approved
0.6864	Remote Similarity	NPD6869	Approved
0.686	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7983	Approved
0.6842	Remote Similarity	NPD5174	Approved
0.6842	Remote Similarity	NPD5175	Approved
0.6838	Remote Similarity	NPD6012	Approved
0.6838	Remote Similarity	NPD6014	Approved
0.6838	Remote Similarity	NPD6013	Approved
0.6822	Remote Similarity	NPD6101	Approved
0.6822	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5695	Phase 3
0.6818	Remote Similarity	NPD5210	Approved
0.6818	Remote Similarity	NPD4629	Approved
0.6814	Remote Similarity	NPD5223	Approved
0.6807	Remote Similarity	NPD6882	Approved
0.6797	Remote Similarity	NPD7319	Approved
0.6789	Remote Similarity	NPD4202	Approved
0.6786	Remote Similarity	NPD5696	Approved
0.6783	Remote Similarity	NPD5141	Approved
0.6765	Remote Similarity	NPD4695	Discontinued
0.6757	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5222	Approved
0.6757	Remote Similarity	NPD5221	Approved
0.6752	Remote Similarity	NPD6011	Approved
0.6729	Remote Similarity	NPD6903	Approved
0.6727	Remote Similarity	NPD7900	Approved
0.6727	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4767	Approved
0.6724	Remote Similarity	NPD4768	Approved
0.6723	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6009	Approved
0.6698	Remote Similarity	NPD7334	Approved
0.6698	Remote Similarity	NPD7521	Approved
0.6698	Remote Similarity	NPD6684	Approved
0.6698	Remote Similarity	NPD6409	Approved
0.6698	Remote Similarity	NPD7146	Approved
0.6698	Remote Similarity	NPD5330	Approved
0.6698	Remote Similarity	NPD5279	Phase 3
0.6697	Remote Similarity	NPD7515	Phase 2
0.6696	Remote Similarity	NPD4754	Approved
0.6696	Remote Similarity	NPD5173	Approved
0.6695	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.664	Remote Similarity	NPD5983	Phase 2
0.664	Remote Similarity	NPD8513	Phase 3
0.664	Remote Similarity	NPD8516	Approved
0.664	Remote Similarity	NPD8515	Approved
0.664	Remote Similarity	NPD8517	Approved
0.6636	Remote Similarity	NPD7524	Approved
0.6635	Remote Similarity	NPD4221	Approved
0.6635	Remote Similarity	NPD4223	Phase 3
0.6615	Remote Similarity	NPD5956	Approved
0.6613	Remote Similarity	NPD4522	Approved
0.661	Remote Similarity	NPD5128	Approved
0.661	Remote Similarity	NPD4730	Approved
0.661	Remote Similarity	NPD4729	Approved
0.6606	Remote Similarity	NPD6698	Approved
0.6606	Remote Similarity	NPD46	Approved
0.6604	Remote Similarity	NPD5329	Approved
0.6574	Remote Similarity	NPD5737	Approved
0.6574	Remote Similarity	NPD6672	Approved
0.6574	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6110	Phase 1
0.6562	Remote Similarity	NPD6336	Discontinued
0.6545	Remote Similarity	NPD5284	Approved
0.6545	Remote Similarity	NPD5281	Approved
0.6535	Remote Similarity	NPD6067	Discontinued
0.6509	Remote Similarity	NPD3668	Phase 3
0.6509	Remote Similarity	NPD4197	Approved
0.6509	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD6274	Approved
0.65	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5251	Approved
0.65	Remote Similarity	NPD5247	Approved
0.65	Remote Similarity	NPD5250	Approved
0.65	Remote Similarity	NPD5249	Phase 3
0.65	Remote Similarity	NPD5248	Approved
0.6491	Remote Similarity	NPD7638	Approved
0.648	Remote Similarity	NPD7100	Approved
0.648	Remote Similarity	NPD7101	Approved
0.6476	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5207	Approved
0.6446	Remote Similarity	NPD5216	Approved
0.6446	Remote Similarity	NPD5217	Approved
0.6446	Remote Similarity	NPD5215	Approved
0.6435	Remote Similarity	NPD7640	Approved
0.6435	Remote Similarity	NPD7639	Approved
0.6415	Remote Similarity	NPD6695	Phase 3
0.6415	Remote Similarity	NPD4788	Approved
0.6408	Remote Similarity	NPD3617	Approved
0.64	Remote Similarity	NPD6335	Approved
0.6396	Remote Similarity	NPD7637	Suspended
0.6389	Remote Similarity	NPD4138	Approved
0.6389	Remote Similarity	NPD4688	Approved
0.6389	Remote Similarity	NPD4693	Phase 3
0.6389	Remote Similarity	NPD4690	Approved
0.6389	Remote Similarity	NPD4689	Approved
0.6389	Remote Similarity	NPD5205	Approved
0.6389	Remote Similarity	NPD5690	Phase 2
0.6389	Remote Similarity	NPD4623	Approved
0.6389	Remote Similarity	NPD4519	Discontinued
0.6389	Remote Similarity	NPD4694	Approved
0.6389	Remote Similarity	NPD5280	Approved
0.6385	Remote Similarity	NPD8074	Phase 3
0.6381	Remote Similarity	NPD5369	Approved
0.6378	Remote Similarity	NPD6908	Approved
0.6378	Remote Similarity	NPD6909	Approved
0.6364	Remote Similarity	NPD6673	Approved
0.6364	Remote Similarity	NPD5135	Approved
0.6364	Remote Similarity	NPD6904	Approved
0.6364	Remote Similarity	NPD5169	Approved
0.6364	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6080	Approved
0.6364	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.633	Remote Similarity	NPD7750	Discontinued
0.633	Remote Similarity	NPD3573	Approved
0.6328	Remote Similarity	NPD8080	Discontinued
0.6321	Remote Similarity	NPD6435	Approved
0.632	Remote Similarity	NPD6317	Approved
0.6316	Remote Similarity	NPD7260	Phase 2

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