NPASS Compound

Structure

NPC265563 OpenBabel07101719512D 45 51 0 0 1 0 0 0 0 0999 V2000 1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 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 3.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 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 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 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 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 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 -4.3301 -1.5000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -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 -2.0000 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 2 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 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 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 17 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 36 1 0 0 0 0 5 36 1 0 0 0 0 6 40 1 0 0 0 0 7 41 1 0 0 0 0 8 42 1 0 0 0 0 9 43 1 0 0 0 0 10 17 2 0 0 0 0 10 23 1 0 0 0 0 11 18 2 0 0 0 0 11 24 1 0 0 0 0 12 20 2 0 0 0 0 12 30 1 0 0 0 0 13 22 1 0 0 0 0 13 28 2 0 0 0 0 14 21 1 0 0 0 0 14 31 2 0 0 0 0 15 25 1 0 0 0 0 15 29 2 0 0 0 0 16 26 2 0 0 0 0 16 27 1 0 0 0 0 17 29 1 0 0 0 0 18 28 1 0 0 0 0 19 20 1 0 0 0 0 19 33 2 0 0 0 0 20 21 1 0 0 0 0 21 22 2 0 0 0 0 22 24 1 0 0 0 0 23 25 1 0 0 0 0 23 27 2 0 0 0 0 24 30 2 0 0 0 0 25 32 2 0 0 0 0 26 32 1 0 0 0 0 26 36 1 0 0 0 0 27 38 1 0 0 0 0 28 40 1 0 0 0 0 29 41 1 0 0 0 0 30 42 1 0 0 0 0 31 33 1 0 0 0 0 31 44 1 0 0 0 0 32 34 1 0 0 0 0 33 45 1 0 0 0 0 34 37 1 1 0 0 0 34 44 1 0 0 0 0 35 36 1 0 0 0 0 35 37 1 0 0 0 0 35 39 2 0 0 0 0 37 43 1 6 0 0 0 37 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	608.24
Volume:	624.661
LogP:	7.703
LogD:	4.594
LogS:	-8.443
# Rotatable Bonds:	4
TPSA:	92.68
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.21
Synthetic Accessibility Score:	4.276
Fsp3:	0.324
Lipinski Rule-of-5:	Rejected
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:	-6.068
MDCK Permeability:	3.036503039766103e-05
Pgp-inhibitor:	0.978
Pgp-substrate:	0.527
Human Intestinal Absorption (HIA):	0.316
20% Bioavailability (F20%):	0.81
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	83.80889129638672%
Volume Distribution (VD):	0.314
Pgp-substrate:	2.7672040462493896%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.989
CYP2C19-inhibitor:	0.367
CYP2C19-substrate:	0.922
CYP2C9-inhibitor:	0.525
CYP2C9-substrate:	0.862
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.927
CYP3A4-inhibitor:	0.496
CYP3A4-substrate:	0.935

ADMET: Excretion

Clearance (CL):	7.839
Half-life (T1/2):	0.068

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.856
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.3
Rat Oral Acute Toxicity:	0.927
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.931
Carcinogencity:	0.369
Eye Corrosion:	0.003
Eye Irritation:	0.868
Respiratory Toxicity:	0.673

Download Data

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

Natural Product: NPC265563

Natural Product ID:	NPC265563
*Common Name:**	BTWUONYKONENGB-ZLHGTEGGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BTWUONYKONENGB-ZLHGTEGGSA-N
Standard InCHI:	InChI=1S/C37H36O8/c1-17-10-23-25(15-29(17)41-7)32-26(16-27(23)38)36(4,5)35(39)37(43-9)34(32)44-31-14-21-20(19(3)33(31)45-37)12-30(42-8)24-11-18(2)28(40-6)13-22(21)24/h10-16,34,38H,1-9H3/t34-,37-/m1/s1
SMILES:	Cc1cc2c(cc1OC)c1c(cc2O)C(C)(C)C(=O)[C@]2([C@@H]1Oc1cc3c(cc(c4cc(C)c(cc34)OC)OC)c(C)c1O2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2409520
PubChem CID:	71746632
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0003007] Phenanthrols

*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
NPO6431	Strophioblachia fimbricalyx	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[19778068]
NPO6431	Strophioblachia fimbricalyx	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23806014]
NPO6431	Strophioblachia fimbricalyx	Species	Euphorbiaceae	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	4

Activity Type	# Activity
Cell Line	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	>	10000.0	nM	PMID[558524]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[558524]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10000.0	nM	PMID[558524]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	>	10000.0	nM	PMID[558524]

☑ 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 NPC265563 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	418
0.1-0.2	1733
0.2-0.3	3627
0.3-0.4	9198
0.4-0.5	9424
0.5-0.6	4168
0.6-0.7	7182
0.7-0.8	6794
0.8-0.85	137
0.85-0.9	8
0.9-0.95	0
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC304125
0.8671	High Similarity	NPC47191
0.8644	High Similarity	NPC205721
0.8563	High Similarity	NPC470334
0.8547	High Similarity	NPC472639
0.8514	High Similarity	NPC184485
0.8514	High Similarity	NPC88739
0.8497	Intermediate Similarity	NPC470335
0.8497	Intermediate Similarity	NPC470336
0.8439	Intermediate Similarity	NPC472638
0.8418	Intermediate Similarity	NPC293227
0.8418	Intermediate Similarity	NPC473717
0.8418	Intermediate Similarity	NPC475662
0.8418	Intermediate Similarity	NPC473631
0.8418	Intermediate Similarity	NPC476203
0.8412	Intermediate Similarity	NPC25889
0.8391	Intermediate Similarity	NPC199357
0.8343	Intermediate Similarity	NPC470667
0.8333	Intermediate Similarity	NPC4200
0.8324	Intermediate Similarity	NPC473686
0.8324	Intermediate Similarity	NPC221140
0.8324	Intermediate Similarity	NPC475220
0.8324	Intermediate Similarity	NPC475352
0.8324	Intermediate Similarity	NPC229817
0.8295	Intermediate Similarity	NPC216307
0.8295	Intermediate Similarity	NPC289876
0.8287	Intermediate Similarity	NPC314672
0.8287	Intermediate Similarity	NPC201814
0.8286	Intermediate Similarity	NPC203751
0.8278	Intermediate Similarity	NPC64755
0.8276	Intermediate Similarity	NPC52598
0.8274	Intermediate Similarity	NPC288353
0.8261	Intermediate Similarity	NPC3474
0.8246	Intermediate Similarity	NPC469472
0.8242	Intermediate Similarity	NPC264302
0.8239	Intermediate Similarity	NPC186800
0.8235	Intermediate Similarity	NPC65784
0.8229	Intermediate Similarity	NPC478002
0.8222	Intermediate Similarity	NPC87583
0.8222	Intermediate Similarity	NPC112380
0.8218	Intermediate Similarity	NPC186100
0.8218	Intermediate Similarity	NPC300307
0.8218	Intermediate Similarity	NPC216403
0.8218	Intermediate Similarity	NPC41494
0.8212	Intermediate Similarity	NPC478001
0.8202	Intermediate Similarity	NPC212290
0.8202	Intermediate Similarity	NPC299149
0.8202	Intermediate Similarity	NPC244903
0.8202	Intermediate Similarity	NPC114257
0.8202	Intermediate Similarity	NPC277710
0.8202	Intermediate Similarity	NPC58538
0.8202	Intermediate Similarity	NPC153578
0.8198	Intermediate Similarity	NPC474240
0.8192	Intermediate Similarity	NPC102053
0.8182	Intermediate Similarity	NPC213052
0.8182	Intermediate Similarity	NPC85368
0.8177	Intermediate Similarity	NPC260521
0.8177	Intermediate Similarity	NPC475179
0.8177	Intermediate Similarity	NPC65489
0.8177	Intermediate Similarity	NPC469649
0.8177	Intermediate Similarity	NPC105591
0.8172	Intermediate Similarity	NPC174140
0.8162	Intermediate Similarity	NPC189312
0.8161	Intermediate Similarity	NPC469521
0.8156	Intermediate Similarity	NPC85316
0.8156	Intermediate Similarity	NPC197357
0.8156	Intermediate Similarity	NPC6709
0.8152	Intermediate Similarity	NPC476358
0.815	Intermediate Similarity	NPC469664
0.815	Intermediate Similarity	NPC475888
0.8146	Intermediate Similarity	NPC478000
0.814	Intermediate Similarity	NPC15374
0.814	Intermediate Similarity	NPC476200
0.814	Intermediate Similarity	NPC192258
0.8136	Intermediate Similarity	NPC146803
0.8136	Intermediate Similarity	NPC473630
0.8132	Intermediate Similarity	NPC223534
0.8132	Intermediate Similarity	NPC158214
0.8132	Intermediate Similarity	NPC240200
0.8132	Intermediate Similarity	NPC290289
0.8132	Intermediate Similarity	NPC473618
0.8129	Intermediate Similarity	NPC299436
0.8129	Intermediate Similarity	NPC141574
0.8122	Intermediate Similarity	NPC104910
0.8122	Intermediate Similarity	NPC474093
0.8114	Intermediate Similarity	NPC259905
0.8114	Intermediate Similarity	NPC475212
0.8111	Intermediate Similarity	NPC150977
0.8111	Intermediate Similarity	NPC321916
0.8111	Intermediate Similarity	NPC313452
0.8103	Intermediate Similarity	NPC477835
0.8103	Intermediate Similarity	NPC272502
0.8103	Intermediate Similarity	NPC178851
0.8101	Intermediate Similarity	NPC120102
0.8098	Intermediate Similarity	NPC314459
0.8098	Intermediate Similarity	NPC470199
0.8095	Intermediate Similarity	NPC475227
0.8095	Intermediate Similarity	NPC200645
0.8095	Intermediate Similarity	NPC106669
0.8092	Intermediate Similarity	NPC173729
0.8092	Intermediate Similarity	NPC290160
0.8092	Intermediate Similarity	NPC223006
0.8092	Intermediate Similarity	NPC134047
0.8092	Intermediate Similarity	NPC272750
0.8092	Intermediate Similarity	NPC197168
0.809	Intermediate Similarity	NPC46958
0.809	Intermediate Similarity	NPC92403
0.809	Intermediate Similarity	NPC66820
0.809	Intermediate Similarity	NPC475054
0.809	Intermediate Similarity	NPC170018
0.809	Intermediate Similarity	NPC76112
0.8087	Intermediate Similarity	NPC93065
0.8087	Intermediate Similarity	NPC31208
0.8087	Intermediate Similarity	NPC472721
0.8087	Intermediate Similarity	NPC187632
0.8087	Intermediate Similarity	NPC472724
0.8087	Intermediate Similarity	NPC160543
0.8087	Intermediate Similarity	NPC469652
0.8087	Intermediate Similarity	NPC472720
0.8081	Intermediate Similarity	NPC18380
0.8081	Intermediate Similarity	NPC472153
0.8081	Intermediate Similarity	NPC189552
0.8081	Intermediate Similarity	NPC474239
0.8081	Intermediate Similarity	NPC273467
0.8079	Intermediate Similarity	NPC131862
0.8077	Intermediate Similarity	NPC179947
0.8077	Intermediate Similarity	NPC269625
0.8072	Intermediate Similarity	NPC474556
0.8072	Intermediate Similarity	NPC472839
0.807	Intermediate Similarity	NPC195167
0.807	Intermediate Similarity	NPC472156
0.8068	Intermediate Similarity	NPC298778
0.8068	Intermediate Similarity	NPC265214
0.8068	Intermediate Similarity	NPC476365
0.8068	Intermediate Similarity	NPC91043
0.8066	Intermediate Similarity	NPC231254
0.8066	Intermediate Similarity	NPC318119
0.8066	Intermediate Similarity	NPC292706
0.8066	Intermediate Similarity	NPC75574
0.8066	Intermediate Similarity	NPC224557
0.8057	Intermediate Similarity	NPC218226
0.8057	Intermediate Similarity	NPC474024
0.8056	Intermediate Similarity	NPC315221
0.8046	Intermediate Similarity	NPC25361
0.8046	Intermediate Similarity	NPC75944
0.8046	Intermediate Similarity	NPC477840
0.8045	Intermediate Similarity	NPC267549
0.8045	Intermediate Similarity	NPC246877
0.8045	Intermediate Similarity	NPC477895
0.8043	Intermediate Similarity	NPC40078
0.8043	Intermediate Similarity	NPC471091
0.8043	Intermediate Similarity	NPC97924
0.8037	Intermediate Similarity	NPC201297
0.8036	Intermediate Similarity	NPC306011
0.8036	Intermediate Similarity	NPC472838
0.8035	Intermediate Similarity	NPC211107
0.8035	Intermediate Similarity	NPC216752
0.8035	Intermediate Similarity	NPC326278
0.8035	Intermediate Similarity	NPC144557
0.8035	Intermediate Similarity	NPC174311
0.8035	Intermediate Similarity	NPC475144
0.8035	Intermediate Similarity	NPC201800
0.8034	Intermediate Similarity	NPC63105
0.8034	Intermediate Similarity	NPC294629
0.8034	Intermediate Similarity	NPC108202
0.8034	Intermediate Similarity	NPC99591
0.8024	Intermediate Similarity	NPC183380
0.8023	Intermediate Similarity	NPC30432
0.8023	Intermediate Similarity	NPC476370
0.8023	Intermediate Similarity	NPC76128
0.8023	Intermediate Similarity	NPC257667
0.8023	Intermediate Similarity	NPC292863
0.8023	Intermediate Similarity	NPC5029
0.8023	Intermediate Similarity	NPC477529
0.8023	Intermediate Similarity	NPC271385
0.8023	Intermediate Similarity	NPC477836
0.8023	Intermediate Similarity	NPC186847
0.8023	Intermediate Similarity	NPC312993
0.8023	Intermediate Similarity	NPC111536
0.8023	Intermediate Similarity	NPC186325
0.8023	Intermediate Similarity	NPC184326
0.8023	Intermediate Similarity	NPC472454
0.8022	Intermediate Similarity	NPC261623
0.8022	Intermediate Similarity	NPC111490
0.8022	Intermediate Similarity	NPC241847
0.8022	Intermediate Similarity	NPC469650
0.8012	Intermediate Similarity	NPC470757
0.8011	Intermediate Similarity	NPC264063
0.8011	Intermediate Similarity	NPC132111
0.8011	Intermediate Similarity	NPC470195
0.8011	Intermediate Similarity	NPC470193
0.8011	Intermediate Similarity	NPC470200
0.8011	Intermediate Similarity	NPC470194
0.8011	Intermediate Similarity	NPC316274
0.8011	Intermediate Similarity	NPC470332
0.8011	Intermediate Similarity	NPC469486
0.8011	Intermediate Similarity	NPC470196
0.8011	Intermediate Similarity	NPC67424
0.8011	Intermediate Similarity	NPC470197
0.8011	Intermediate Similarity	NPC282474

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 NPC265563 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	377
0.1-0.2	986
0.2-0.3	1814
0.3-0.4	2658
0.4-0.5	1823
0.5-0.6	927
0.6-0.7	441
0.7-0.8	121
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8475	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6959	Discontinued
0.809	Intermediate Similarity	NPD8313	Approved
0.809	Intermediate Similarity	NPD8312	Approved
0.8034	Intermediate Similarity	NPD7808	Phase 3
0.7978	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD6166	Phase 2
0.7941	Intermediate Similarity	NPD8455	Phase 2
0.7931	Intermediate Similarity	NPD3787	Discontinued
0.791	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD5844	Phase 1
0.7898	Intermediate Similarity	NPD7473	Discontinued
0.7877	Intermediate Similarity	NPD7251	Discontinued
0.7865	Intermediate Similarity	NPD7074	Phase 3
0.7829	Intermediate Similarity	NPD6232	Discontinued
0.7821	Intermediate Similarity	NPD6797	Phase 2
0.7811	Intermediate Similarity	NPD7458	Discontinued
0.7809	Intermediate Similarity	NPD7054	Approved
0.7802	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7472	Approved
0.7722	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7075	Discontinued
0.7688	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7228	Approved
0.7654	Intermediate Similarity	NPD3751	Discontinued
0.764	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7819	Suspended
0.763	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD7871	Phase 2
0.7617	Intermediate Similarity	NPD7870	Phase 2
0.759	Intermediate Similarity	NPD6674	Discontinued
0.7572	Intermediate Similarity	NPD37	Approved
0.7572	Intermediate Similarity	NPD1934	Approved
0.7571	Intermediate Similarity	NPD7199	Phase 2
0.7557	Intermediate Similarity	NPD6234	Discontinued
0.7551	Intermediate Similarity	NPD8151	Discontinued
0.7543	Intermediate Similarity	NPD4966	Approved
0.7543	Intermediate Similarity	NPD4967	Phase 2
0.7543	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD4965	Approved
0.7529	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6559	Discontinued
0.7486	Intermediate Similarity	NPD3817	Phase 2
0.7474	Intermediate Similarity	NPD7697	Approved
0.7474	Intermediate Similarity	NPD7696	Phase 3
0.7474	Intermediate Similarity	NPD7435	Discontinued
0.7474	Intermediate Similarity	NPD7698	Approved
0.7472	Intermediate Similarity	NPD8127	Discontinued
0.7459	Intermediate Similarity	NPD3818	Discontinued
0.7443	Intermediate Similarity	NPD7768	Phase 2
0.7443	Intermediate Similarity	NPD3882	Suspended
0.744	Intermediate Similarity	NPD7003	Approved
0.7412	Intermediate Similarity	NPD7390	Discontinued
0.741	Intermediate Similarity	NPD6100	Approved
0.741	Intermediate Similarity	NPD6099	Approved
0.7409	Intermediate Similarity	NPD6780	Approved
0.7409	Intermediate Similarity	NPD6778	Approved
0.7409	Intermediate Similarity	NPD6782	Approved
0.7409	Intermediate Similarity	NPD6779	Approved
0.7409	Intermediate Similarity	NPD6781	Approved
0.7409	Intermediate Similarity	NPD6777	Approved
0.7409	Intermediate Similarity	NPD6776	Approved
0.7401	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6599	Discontinued
0.7337	Intermediate Similarity	NPD8166	Discontinued
0.7337	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7874	Approved
0.7337	Intermediate Similarity	NPD4628	Phase 3
0.7323	Intermediate Similarity	NPD7701	Phase 2
0.7318	Intermediate Similarity	NPD5494	Approved
0.7317	Intermediate Similarity	NPD4060	Phase 1
0.7314	Intermediate Similarity	NPD7411	Suspended
0.7301	Intermediate Similarity	NPD6798	Discontinued
0.73	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7783	Phase 2
0.7299	Intermediate Similarity	NPD3226	Approved
0.7297	Intermediate Similarity	NPD7240	Approved
0.7287	Intermediate Similarity	NPD8150	Discontinued
0.7278	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6801	Discontinued
0.7267	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD2490	Approved
0.7263	Intermediate Similarity	NPD2488	Approved
0.7257	Intermediate Similarity	NPD4380	Phase 2
0.7232	Intermediate Similarity	NPD1465	Phase 2
0.7232	Intermediate Similarity	NPD2801	Approved
0.7216	Intermediate Similarity	NPD7700	Phase 2
0.7216	Intermediate Similarity	NPD7699	Phase 2
0.7214	Intermediate Similarity	NPD7801	Approved
0.72	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7177	Discontinued
0.7172	Intermediate Similarity	NPD8319	Approved
0.7172	Intermediate Similarity	NPD8320	Phase 1
0.7169	Intermediate Similarity	NPD6355	Discontinued
0.7168	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD6535	Approved
0.715	Intermediate Similarity	NPD6534	Approved
0.7134	Intermediate Similarity	NPD7095	Approved
0.7128	Intermediate Similarity	NPD2971	Approved
0.7128	Intermediate Similarity	NPD2968	Approved
0.7126	Intermediate Similarity	NPD1512	Approved
0.7111	Intermediate Similarity	NPD3749	Approved
0.7107	Intermediate Similarity	NPD2493	Approved
0.7107	Intermediate Similarity	NPD2494	Approved
0.7105	Intermediate Similarity	NPD8434	Phase 2
0.7086	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7097	Phase 1
0.7077	Intermediate Similarity	NPD2975	Approved
0.7077	Intermediate Similarity	NPD2974	Approved
0.7077	Intermediate Similarity	NPD2973	Approved
0.7072	Intermediate Similarity	NPD919	Approved
0.7071	Intermediate Similarity	NPD6823	Phase 2
0.7059	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2346	Discontinued
0.7059	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4110	Phase 3
0.7029	Intermediate Similarity	NPD6273	Approved
0.7026	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7685	Pre-registration
0.702	Intermediate Similarity	NPD3452	Approved
0.702	Intermediate Similarity	NPD3450	Approved
0.7018	Intermediate Similarity	NPD1549	Phase 2
0.7011	Intermediate Similarity	NPD3926	Phase 2
0.7011	Intermediate Similarity	NPD1511	Approved
0.7011	Intermediate Similarity	NPD6799	Approved
0.7	Intermediate Similarity	NPD4582	Approved
0.7	Intermediate Similarity	NPD5408	Approved
0.7	Intermediate Similarity	NPD5405	Approved
0.7	Intermediate Similarity	NPD5404	Approved
0.7	Intermediate Similarity	NPD2438	Suspended
0.7	Intermediate Similarity	NPD5406	Approved
0.7	Intermediate Similarity	NPD4583	Approved
0.6988	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD2532	Approved
0.6971	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD2534	Approved
0.6971	Remote Similarity	NPD2533	Approved
0.697	Remote Similarity	NPD4580	Approved
0.6966	Remote Similarity	NPD7028	Phase 2
0.6959	Remote Similarity	NPD5763	Approved
0.6959	Remote Similarity	NPD5762	Approved
0.6957	Remote Similarity	NPD7229	Phase 3
0.695	Remote Similarity	NPD4004	Approved
0.695	Remote Similarity	NPD4002	Approved
0.695	Remote Similarity	NPD7680	Approved
0.6946	Remote Similarity	NPD8032	Phase 2
0.6946	Remote Similarity	NPD6233	Phase 2
0.6933	Remote Similarity	NPD1283	Approved
0.6928	Remote Similarity	NPD4625	Phase 3
0.6919	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5402	Approved
0.6905	Remote Similarity	NPD3620	Phase 2
0.6905	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD1247	Approved
0.6897	Remote Similarity	NPD6190	Approved
0.6893	Remote Similarity	NPD5403	Approved
0.6886	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1651	Approved
0.6867	Remote Similarity	NPD4908	Phase 1
0.6859	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7033	Discontinued
0.6839	Remote Similarity	NPD3750	Approved
0.6837	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6213	Phase 3
0.6837	Remote Similarity	NPD6212	Phase 3
0.6825	Remote Similarity	NPD7907	Approved
0.6823	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2897	Discontinued
0.6816	Remote Similarity	NPD3057	Approved
0.681	Remote Similarity	NPD1608	Approved
0.6805	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD2979	Phase 3
0.6805	Remote Similarity	NPD1613	Approved
0.6802	Remote Similarity	NPD2796	Approved
0.6798	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD5709	Phase 3
0.6786	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5401	Approved
0.6765	Remote Similarity	NPD1933	Approved
0.6763	Remote Similarity	NPD7266	Discontinued
0.6763	Remote Similarity	NPD2344	Approved
0.6757	Remote Similarity	NPD4666	Phase 3
0.6749	Remote Similarity	NPD4040	Phase 1
0.6748	Remote Similarity	NPD1281	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