NPASS Compound

Structure

NPC250687 OpenBabel07101719142D 35 38 0 0 1 0 0 0 0 0999 V2000 -6.8059 -2.5361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6497 -1.0746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4034 0.1756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5352 -0.2668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6311 -2.4056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3996 0.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2744 1.8485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9186 -0.6251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6054 -5.7809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5868 -1.0746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4306 -1.5618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9621 -0.1002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2590 1.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0825 1.5744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1183 -3.2494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6054 -2.4056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2280 1.3400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1183 0.3870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8586 1.3222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8059 -1.5618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9621 -1.0746 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5868 -0.1002 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8627 0.5518 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2744 -1.0746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6132 0.7572 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6054 -4.0932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5862 0.7062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1183 -1.5618 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4306 0.3870 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2744 -0.1002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9096 0.3492 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5798 -4.0932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1169 1.5234 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1183 -4.9370 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 20 2 0 0 0 0 2 20 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 9 34 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 24 1 0 0 0 0 12 18 1 0 0 0 0 12 21 1 0 0 0 0 13 17 1 0 0 0 0 14 19 1 0 0 0 0 14 25 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 20 21 1 0 0 0 0 21 28 1 6 0 0 0 22 23 1 0 0 0 0 22 29 1 1 0 0 0 23 13 1 6 0 0 0 23 31 1 0 0 0 0 24 28 1 6 0 0 0 24 30 1 0 0 0 0 25 27 1 6 0 0 0 25 35 1 0 0 0 0 26 32 2 0 0 0 0 26 34 1 0 0 0 0 27 33 1 0 0 0 0 28 5 1 6 0 0 0 29 30 1 6 0 0 0 30 7 1 6 0 0 0 31 8 1 1 0 0 0 31 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.39
Volume:	540.394
LogP:	6.486
LogD:	5.073
LogS:	-5.548
# Rotatable Bonds:	7
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.32
Synthetic Accessibility Score:	4.886
Fsp3:	0.903
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:	-4.761
MDCK Permeability:	1.9302964574308135e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.213
30% Bioavailability (F30%):	0.792

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	91.2884292602539%
Volume Distribution (VD):	1.006
Pgp-substrate:	2.9179725646972656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.408
CYP2C19-inhibitor:	0.072
CYP2C19-substrate:	0.951
CYP2C9-inhibitor:	0.191
CYP2C9-substrate:	0.154
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.456
CYP3A4-inhibitor:	0.715
CYP3A4-substrate:	0.551

ADMET: Excretion

Clearance (CL):	6.078
Half-life (T1/2):	0.088

ADMET: Toxicity

hERG Blockers:	0.696
Human Hepatotoxicity (H-HT):	0.346
Drug-inuced Liver Injury (DILI):	0.275
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.082
Maximum Recommended Daily Dose:	0.067
Skin Sensitization:	0.952
Carcinogencity:	0.058
Eye Corrosion:	0.17
Eye Irritation:	0.036
Respiratory Toxicity:	0.914

Download Data

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

Natural Product: NPC250687

Natural Product ID:	NPC250687
*Common Name:**	Methyl Shoreate
IUPAC Name:	methyl 3-[(3S,3aR,5aR,6S,7S,9aR,9bR)-3-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-prop-1-en-2-yl-1,2,3,3a,4,5,5a,7,8,9-decahydrocyclopenta[a]naphthalen-6-yl]propanoate
Synonyms:	Methyl Shoreate
Standard InCHIKey:	TWFMQZXDUHCZFN-SRACOBAWSA-N
Standard InCHI:	InChI=1S/C31H52O4/c1-20(2)21-12-18-30(7)24(28(21,5)16-15-26(32)34-9)11-10-22-23(13-17-29(22,30)6)31(8)19-14-25(35-31)27(3,4)33/h21-25,33H,1,10-19H2,2-9H3/t21-,22+,23-,24+,25+,28-,29+,30+,31-/m0/s1
SMILES:	C=C(C)[C@@H]1CC[C@]2(C)[C@H](CC[C@@H]3[C@H](CC[C@@]23C)[C@]2(C)CC[C@H](C(C)(C)O)O2)[C@@]1(C)CCC(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL387861
PubChem CID:	44421646
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001755] Diterpene 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
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	floral spikes	n.a.	n.a.	PMID[17346076]
NPO32464	dysoxylum binecteriferum	Species	Meliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[24547740]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[9873651]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4138.1	Betula platyphylla var. japonica	Varieties	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	12

Activity Type	# Activity
Cell Line	8
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	66600.0	nM	PMID[512147]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	20100.0	nM	PMID[512147]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	59700.0	nM	PMID[512147]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	67700.0	nM	PMID[512147]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	6300.0	nM	PMID[512148]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	5600.0	nM	PMID[512148]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	12900.0	nM	PMID[512148]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[512148]
NPT27	Others	Unspecified		IC50	=	93500.0	nM	PMID[512147]
NPT27	Others	Unspecified		IC50	=	20100.0	nM	PMID[512147]
NPT27	Others	Unspecified		IC50	=	50900.0	nM	PMID[512147]
NPT27	Others	Unspecified		IC50	=	47100.0	nM	PMID[512147]

☑ 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 NPC250687 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	188
0.1-0.2	1342
0.2-0.3	5982
0.3-0.4	15366
0.4-0.5	6018
0.5-0.6	5719
0.6-0.7	6689
0.7-0.8	1316
0.8-0.85	55
0.85-0.9	13
0.9-0.95	3
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC229407
1.0	High Similarity	NPC254572
1.0	High Similarity	NPC48824
0.988	High Similarity	NPC269267
0.9647	High Similarity	NPC471747
0.9405	High Similarity	NPC251808
0.9405	High Similarity	NPC474174
0.907	High Similarity	NPC255176
0.8916	High Similarity	NPC232625
0.881	High Similarity	NPC164289
0.881	High Similarity	NPC242771
0.881	High Similarity	NPC102156
0.881	High Similarity	NPC311642
0.881	High Similarity	NPC148740
0.881	High Similarity	NPC100366
0.8795	High Similarity	NPC170038
0.8675	High Similarity	NPC118987
0.8621	High Similarity	NPC475007
0.8542	High Similarity	NPC471293
0.8523	High Similarity	NPC167877
0.8511	High Similarity	NPC167974
0.8495	Intermediate Similarity	NPC253586
0.8488	Intermediate Similarity	NPC471037
0.8351	Intermediate Similarity	NPC255309
0.8316	Intermediate Similarity	NPC108371
0.8283	Intermediate Similarity	NPC224414
0.8283	Intermediate Similarity	NPC258323
0.828	Intermediate Similarity	NPC279974
0.8265	Intermediate Similarity	NPC96377
0.8261	Intermediate Similarity	NPC291373
0.8235	Intermediate Similarity	NPC245029
0.8235	Intermediate Similarity	NPC31302
0.8222	Intermediate Similarity	NPC4309
0.8214	Intermediate Similarity	NPC66105
0.8202	Intermediate Similarity	NPC80590
0.8202	Intermediate Similarity	NPC472505
0.8182	Intermediate Similarity	NPC100391
0.8182	Intermediate Similarity	NPC59530
0.8172	Intermediate Similarity	NPC277399
0.8163	Intermediate Similarity	NPC100955
0.8163	Intermediate Similarity	NPC121566
0.8144	Intermediate Similarity	NPC94919
0.8132	Intermediate Similarity	NPC220498
0.8132	Intermediate Similarity	NPC253618
0.8132	Intermediate Similarity	NPC215029
0.8132	Intermediate Similarity	NPC476733
0.8132	Intermediate Similarity	NPC77001
0.8119	Intermediate Similarity	NPC106760
0.8119	Intermediate Similarity	NPC101450
0.8118	Intermediate Similarity	NPC321690
0.8111	Intermediate Similarity	NPC134197
0.8111	Intermediate Similarity	NPC33768
0.81	Intermediate Similarity	NPC255082
0.8095	Intermediate Similarity	NPC476601
0.8095	Intermediate Similarity	NPC246445
0.8081	Intermediate Similarity	NPC95243
0.8081	Intermediate Similarity	NPC63023
0.8081	Intermediate Similarity	NPC472655
0.8068	Intermediate Similarity	NPC268578
0.8068	Intermediate Similarity	NPC217559
0.8068	Intermediate Similarity	NPC245866
0.8068	Intermediate Similarity	NPC292458
0.8065	Intermediate Similarity	NPC475061
0.8065	Intermediate Similarity	NPC470224
0.8043	Intermediate Similarity	NPC471896
0.8043	Intermediate Similarity	NPC289213
0.8039	Intermediate Similarity	NPC272242
0.8022	Intermediate Similarity	NPC211162
0.8022	Intermediate Similarity	NPC183374
0.8021	Intermediate Similarity	NPC119036
0.8	Intermediate Similarity	NPC2783
0.8	Intermediate Similarity	NPC12774
0.8	Intermediate Similarity	NPC92139
0.8	Intermediate Similarity	NPC70661
0.8	Intermediate Similarity	NPC256227
0.8	Intermediate Similarity	NPC131665
0.8	Intermediate Similarity	NPC255387
0.8	Intermediate Similarity	NPC238227
0.7979	Intermediate Similarity	NPC47853
0.7979	Intermediate Similarity	NPC67831
0.7979	Intermediate Similarity	NPC174051
0.7978	Intermediate Similarity	NPC263974
0.7978	Intermediate Similarity	NPC97505
0.7959	Intermediate Similarity	NPC124544
0.7959	Intermediate Similarity	NPC473928
0.7957	Intermediate Similarity	NPC160506
0.7957	Intermediate Similarity	NPC150383
0.7957	Intermediate Similarity	NPC189520
0.7957	Intermediate Similarity	NPC471901
0.7957	Intermediate Similarity	NPC219516
0.7957	Intermediate Similarity	NPC262870
0.7941	Intermediate Similarity	NPC475134
0.7941	Intermediate Similarity	NPC475563
0.7938	Intermediate Similarity	NPC477655
0.7938	Intermediate Similarity	NPC477656
0.7935	Intermediate Similarity	NPC24772
0.7935	Intermediate Similarity	NPC116146
0.7935	Intermediate Similarity	NPC474889
0.7935	Intermediate Similarity	NPC474570
0.7931	Intermediate Similarity	NPC206735
0.7931	Intermediate Similarity	NPC472853
0.7917	Intermediate Similarity	NPC475894
0.7912	Intermediate Similarity	NPC128644
0.7912	Intermediate Similarity	NPC269360
0.7912	Intermediate Similarity	NPC264005
0.7912	Intermediate Similarity	NPC90652
0.79	Intermediate Similarity	NPC475414
0.79	Intermediate Similarity	NPC173172
0.7895	Intermediate Similarity	NPC470229
0.7895	Intermediate Similarity	NPC98639
0.7889	Intermediate Similarity	NPC98270
0.7889	Intermediate Similarity	NPC470223
0.7889	Intermediate Similarity	NPC264317
0.7889	Intermediate Similarity	NPC201655
0.7889	Intermediate Similarity	NPC294438
0.7885	Intermediate Similarity	NPC102619
0.7882	Intermediate Similarity	NPC20466
0.7879	Intermediate Similarity	NPC209298
0.7879	Intermediate Similarity	NPC36688
0.7879	Intermediate Similarity	NPC474775
0.7879	Intermediate Similarity	NPC221421
0.7879	Intermediate Similarity	NPC140723
0.7879	Intermediate Similarity	NPC277074
0.7872	Intermediate Similarity	NPC287118
0.7872	Intermediate Similarity	NPC244356
0.7872	Intermediate Similarity	NPC471902
0.7872	Intermediate Similarity	NPC224060
0.7872	Intermediate Similarity	NPC473690
0.7865	Intermediate Similarity	NPC170862
0.7865	Intermediate Similarity	NPC239308
0.7864	Intermediate Similarity	NPC475480
0.7864	Intermediate Similarity	NPC475668
0.7864	Intermediate Similarity	NPC473921
0.7857	Intermediate Similarity	NPC252614
0.7849	Intermediate Similarity	NPC148414
0.7849	Intermediate Similarity	NPC175628
0.7849	Intermediate Similarity	NPC111585
0.7843	Intermediate Similarity	NPC170221
0.7843	Intermediate Similarity	NPC10064
0.7843	Intermediate Similarity	NPC284828
0.7843	Intermediate Similarity	NPC173905
0.7843	Intermediate Similarity	NPC472216
0.7843	Intermediate Similarity	NPC5475
0.7841	Intermediate Similarity	NPC223330
0.7841	Intermediate Similarity	NPC190940
0.7841	Intermediate Similarity	NPC327002
0.7841	Intermediate Similarity	NPC209318
0.7835	Intermediate Similarity	NPC153792
0.7835	Intermediate Similarity	NPC472028
0.7835	Intermediate Similarity	NPC473155
0.7835	Intermediate Similarity	NPC271387
0.7826	Intermediate Similarity	NPC16377
0.7826	Intermediate Similarity	NPC470417
0.7826	Intermediate Similarity	NPC474719
0.7826	Intermediate Similarity	NPC28227
0.7822	Intermediate Similarity	NPC287269
0.7822	Intermediate Similarity	NPC475176
0.7816	Intermediate Similarity	NPC471475
0.7816	Intermediate Similarity	NPC192744
0.7812	Intermediate Similarity	NPC322063
0.7812	Intermediate Similarity	NPC42042
0.7812	Intermediate Similarity	NPC329910
0.7812	Intermediate Similarity	NPC29410
0.7812	Intermediate Similarity	NPC200054
0.7802	Intermediate Similarity	NPC155011
0.7802	Intermediate Similarity	NPC80700
0.7802	Intermediate Similarity	NPC474448
0.7802	Intermediate Similarity	NPC324063
0.78	Intermediate Similarity	NPC328737
0.78	Intermediate Similarity	NPC301787
0.7791	Intermediate Similarity	NPC68828
0.7789	Intermediate Similarity	NPC475118
0.7778	Intermediate Similarity	NPC475509
0.7778	Intermediate Similarity	NPC22388
0.7778	Intermediate Similarity	NPC165064
0.7778	Intermediate Similarity	NPC299963
0.7767	Intermediate Similarity	NPC6206
0.7767	Intermediate Similarity	NPC5284
0.7766	Intermediate Similarity	NPC475416
0.7766	Intermediate Similarity	NPC26888
0.7766	Intermediate Similarity	NPC154101
0.7755	Intermediate Similarity	NPC267921
0.7755	Intermediate Similarity	NPC94906
0.7755	Intermediate Similarity	NPC476303
0.7753	Intermediate Similarity	NPC145143
0.7753	Intermediate Similarity	NPC474605
0.7753	Intermediate Similarity	NPC477286
0.7753	Intermediate Similarity	NPC477936
0.7753	Intermediate Similarity	NPC286719
0.7753	Intermediate Similarity	NPC472504
0.7753	Intermediate Similarity	NPC476292
0.7753	Intermediate Similarity	NPC170985
0.7745	Intermediate Similarity	NPC472217
0.7745	Intermediate Similarity	NPC295389
0.7745	Intermediate Similarity	NPC88744
0.7745	Intermediate Similarity	NPC472218
0.7745	Intermediate Similarity	NPC472219
0.7745	Intermediate Similarity	NPC19412
0.7742	Intermediate Similarity	NPC32830
0.7742	Intermediate Similarity	NPC475921

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 NPC250687 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1894
0.2-0.3	4139
0.3-0.4	1974
0.4-0.5	493
0.5-0.6	178
0.6-0.7	246
0.7-0.8	59
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
0.7957	Intermediate Similarity	NPD8035	Phase 2
0.7957	Intermediate Similarity	NPD8034	Phase 2
0.7889	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD6399	Phase 3
0.7551	Intermediate Similarity	NPD6083	Phase 2
0.7551	Intermediate Similarity	NPD6084	Phase 2
0.75	Intermediate Similarity	NPD6114	Approved
0.75	Intermediate Similarity	NPD6118	Approved
0.75	Intermediate Similarity	NPD6697	Approved
0.75	Intermediate Similarity	NPD6115	Approved
0.7473	Intermediate Similarity	NPD4788	Approved
0.7447	Intermediate Similarity	NPD6903	Approved
0.7447	Intermediate Similarity	NPD5737	Approved
0.7447	Intermediate Similarity	NPD6672	Approved
0.7419	Intermediate Similarity	NPD7334	Approved
0.7419	Intermediate Similarity	NPD7521	Approved
0.7419	Intermediate Similarity	NPD6684	Approved
0.7419	Intermediate Similarity	NPD5330	Approved
0.7419	Intermediate Similarity	NPD6409	Approved
0.7419	Intermediate Similarity	NPD7146	Approved
0.7391	Intermediate Similarity	NPD4786	Approved
0.7383	Intermediate Similarity	NPD8133	Approved
0.7356	Intermediate Similarity	NPD3702	Approved
0.7347	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5695	Phase 3
0.7308	Intermediate Similarity	NPD6412	Phase 2
0.73	Intermediate Similarity	NPD5696	Approved
0.73	Intermediate Similarity	NPD7638	Approved
0.7273	Intermediate Similarity	NPD6117	Approved
0.7263	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7320	Approved
0.7234	Intermediate Similarity	NPD6098	Approved
0.7228	Intermediate Similarity	NPD7639	Approved
0.7228	Intermediate Similarity	NPD7640	Approved
0.7222	Intermediate Similarity	NPD4632	Approved
0.7212	Intermediate Similarity	NPD7128	Approved
0.7212	Intermediate Similarity	NPD5739	Approved
0.7212	Intermediate Similarity	NPD6675	Approved
0.7212	Intermediate Similarity	NPD6008	Approved
0.7212	Intermediate Similarity	NPD6402	Approved
0.7191	Intermediate Similarity	NPD6116	Phase 1
0.7188	Intermediate Similarity	NPD6080	Approved
0.7188	Intermediate Similarity	NPD6673	Approved
0.7188	Intermediate Similarity	NPD6904	Approved
0.7174	Intermediate Similarity	NPD3667	Approved
0.7158	Intermediate Similarity	NPD7524	Approved
0.713	Intermediate Similarity	NPD8297	Approved
0.7075	Intermediate Similarity	NPD6686	Approved
0.7075	Intermediate Similarity	NPD6881	Approved
0.7075	Intermediate Similarity	NPD6899	Approved
0.7071	Intermediate Similarity	NPD7748	Approved
0.7043	Intermediate Similarity	NPD7492	Approved
0.7041	Intermediate Similarity	NPD7637	Suspended
0.7027	Intermediate Similarity	NPD7115	Discovery
0.7021	Intermediate Similarity	NPD3133	Approved
0.7021	Intermediate Similarity	NPD3666	Approved
0.7021	Intermediate Similarity	NPD3665	Phase 1
0.7011	Intermediate Similarity	NPD6081	Approved
0.7011	Intermediate Similarity	NPD5777	Approved
0.701	Intermediate Similarity	NPD4753	Phase 2
0.701	Intermediate Similarity	NPD5328	Approved
0.7009	Intermediate Similarity	NPD6372	Approved
0.7009	Intermediate Similarity	NPD6373	Approved
0.6991	Remote Similarity	NPD6059	Approved
0.6991	Remote Similarity	NPD6319	Approved
0.6991	Remote Similarity	NPD6054	Approved
0.6989	Remote Similarity	NPD4223	Phase 3
0.6989	Remote Similarity	NPD4221	Approved
0.6983	Remote Similarity	NPD6616	Approved
0.6983	Remote Similarity	NPD7507	Approved
0.6981	Remote Similarity	NPD5697	Approved
0.6981	Remote Similarity	NPD5701	Approved
0.6947	Remote Similarity	NPD5329	Approved
0.6944	Remote Similarity	NPD7290	Approved
0.6944	Remote Similarity	NPD7102	Approved
0.6944	Remote Similarity	NPD6883	Approved
0.6939	Remote Similarity	NPD5207	Approved
0.6923	Remote Similarity	NPD8293	Discontinued
0.6923	Remote Similarity	NPD7078	Approved
0.6916	Remote Similarity	NPD6011	Approved
0.6916	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6695	Phase 3
0.6907	Remote Similarity	NPD5208	Approved
0.6905	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6001	Approved
0.6889	Remote Similarity	NPD6933	Approved
0.6881	Remote Similarity	NPD6869	Approved
0.6881	Remote Similarity	NPD8130	Phase 1
0.6881	Remote Similarity	NPD6649	Approved
0.6881	Remote Similarity	NPD6650	Approved
0.6881	Remote Similarity	NPD6617	Approved
0.6881	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6847	Approved
0.6875	Remote Similarity	NPD3618	Phase 1
0.6875	Remote Similarity	NPD6009	Approved
0.687	Remote Similarity	NPD6370	Approved
0.6869	Remote Similarity	NPD7515	Phase 2
0.6869	Remote Similarity	NPD6050	Approved
0.6869	Remote Similarity	NPD6079	Approved
0.6869	Remote Similarity	NPD5281	Approved
0.6869	Remote Similarity	NPD5284	Approved
0.6869	Remote Similarity	NPD5693	Phase 1
0.6864	Remote Similarity	NPD7736	Approved
0.6863	Remote Similarity	NPD7902	Approved
0.6852	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6014	Approved
0.6852	Remote Similarity	NPD6012	Approved
0.6852	Remote Similarity	NPD6013	Approved
0.6842	Remote Similarity	NPD3668	Phase 3
0.6842	Remote Similarity	NPD4197	Approved
0.6842	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6051	Approved
0.6824	Remote Similarity	NPD4224	Phase 2
0.6818	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6882	Approved
0.681	Remote Similarity	NPD7604	Phase 2
0.6809	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7319	Approved
0.68	Remote Similarity	NPD4202	Approved
0.6796	Remote Similarity	NPD4225	Approved
0.6783	Remote Similarity	NPD5983	Phase 2
0.6783	Remote Similarity	NPD6016	Approved
0.6783	Remote Similarity	NPD6015	Approved
0.6774	Remote Similarity	NPD7525	Registered
0.6768	Remote Similarity	NPD5692	Phase 3
0.6762	Remote Similarity	NPD7632	Discontinued
0.6739	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5362	Discontinued
0.6724	Remote Similarity	NPD5988	Approved
0.6705	Remote Similarity	NPD4244	Approved
0.6705	Remote Similarity	NPD4245	Approved
0.6705	Remote Similarity	NPD4789	Approved
0.6701	Remote Similarity	NPD4693	Phase 3
0.6701	Remote Similarity	NPD4138	Approved
0.6701	Remote Similarity	NPD4688	Approved
0.6701	Remote Similarity	NPD4690	Approved
0.6701	Remote Similarity	NPD5279	Phase 3
0.6701	Remote Similarity	NPD4689	Approved
0.6701	Remote Similarity	NPD5205	Approved
0.67	Remote Similarity	NPD5694	Approved
0.6699	Remote Similarity	NPD4755	Approved
0.6698	Remote Similarity	NPD6052	Approved
0.6697	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD5360	Phase 3
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4634	Approved
0.6636	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7750	Discontinued
0.6609	Remote Similarity	NPD7516	Approved
0.6602	Remote Similarity	NPD4697	Phase 3
0.6602	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5222	Approved
0.6602	Remote Similarity	NPD5221	Approved
0.6596	Remote Similarity	NPD6931	Approved
0.6596	Remote Similarity	NPD6930	Phase 2
0.6593	Remote Similarity	NPD3703	Phase 2
0.6593	Remote Similarity	NPD7339	Approved
0.6593	Remote Similarity	NPD6942	Approved
0.6591	Remote Similarity	NPD3698	Phase 2
0.6591	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6033	Approved
0.6571	Remote Similarity	NPD5285	Approved
0.6571	Remote Similarity	NPD5286	Approved
0.6571	Remote Similarity	NPD4700	Approved
0.6571	Remote Similarity	NPD4696	Approved
0.6569	Remote Similarity	NPD7900	Approved
0.6569	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD3617	Approved
0.6552	Remote Similarity	NPD8294	Approved
0.6552	Remote Similarity	NPD8377	Approved
0.6538	Remote Similarity	NPD5173	Approved
0.6535	Remote Similarity	NPD6411	Approved
0.6531	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD5690	Phase 2
0.6531	Remote Similarity	NPD5280	Approved
0.6531	Remote Similarity	NPD4694	Approved
0.6526	Remote Similarity	NPD4692	Approved
0.6526	Remote Similarity	NPD5369	Approved
0.6526	Remote Similarity	NPD4139	Approved
0.6525	Remote Similarity	NPD6067	Discontinued
0.6522	Remote Similarity	NPD6335	Approved
0.6514	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5223	Approved
0.6509	Remote Similarity	NPD1700	Approved
0.6496	Remote Similarity	NPD8335	Approved
0.6496	Remote Similarity	NPD8378	Approved
0.6496	Remote Similarity	NPD8033	Approved
0.6496	Remote Similarity	NPD8296	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