NPASS Compound

Structure

CID116639 OpenBabel06191715472D 29 33 0 0 1 0 0 0 0 0999 V2000 -4.6369 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9456 1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9692 0.2463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7922 -1.7645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3590 2.1660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0818 1.4749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3217 1.7730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4784 1.6921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5978 2.1660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6569 0.7082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9990 -0.0449 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 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 0.6426 3.1650 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3920 -0.9644 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6479 0.5740 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 6 28 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 8 18 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 29 1 0 0 0 0 14 17 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 15 26 1 0 0 0 0 16 17 1 0 0 0 0 16 21 2 0 0 0 0 17 27 1 6 0 0 0 18 23 1 0 0 0 0 18 24 1 6 0 0 0 19 25 1 6 0 0 0 19 26 1 0 0 0 0 20 24 1 6 0 0 0 20 25 1 0 0 0 0 21 22 1 0 0 0 0 21 29 1 0 0 0 0 22 26 1 1 0 0 0 22 28 1 0 0 0 0 24 3 1 6 0 0 0 25 4 1 6 0 0 0 26 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.3
Volume:	436.568
LogP:	5.882
LogD:	4.798
LogS:	-5.372
# Rotatable Bonds:	1
TPSA:	42.6
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.572
Synthetic Accessibility Score:	4.939
Fsp3:	0.846
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.802
MDCK Permeability:	1.5508519936702214e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.042
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.329
Plasma Protein Binding (PPB):	92.22767639160156%
Volume Distribution (VD):	1.929
Pgp-substrate:	6.7548370361328125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.339
CYP2C19-inhibitor:	0.065
CYP2C19-substrate:	0.905
CYP2C9-inhibitor:	0.293
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.048
CYP2D6-substrate:	0.467
CYP3A4-inhibitor:	0.556
CYP3A4-substrate:	0.58

ADMET: Excretion

Clearance (CL):	11.422
Half-life (T1/2):	0.054

ADMET: Toxicity

hERG Blockers:	0.221
Human Hepatotoxicity (H-HT):	0.165
Drug-inuced Liver Injury (DILI):	0.105
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.948
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.537
Carcinogencity:	0.328
Eye Corrosion:	0.256
Eye Irritation:	0.612
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC116639

Natural Product ID:	NPC116639
*Common Name:**	Similan A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MRMQROGLXJNWRO-WOHKTHDMSA-N
Standard InCHI:	InChI=1S/C26H40O3/c1-23(2)10-7-11-24(3)18(23)8-12-25(4)19-14-17(27)16-9-13-29-21(16)22(28-6)26(19,5)15-20(24)25/h9,13,17-20,22,27H,7-8,10-12,14-15H2,1-6H3/t17-,18-,19-,20+,22+,24-,25-,26-/m0/s1
SMILES:	CC1(C)CCC[C@@]2(C)[C@H]1CC[C@@]1(C)[C@@H]3C[C@@H](c4ccoc4[C@H]([C@@]3(C)C[C@H]21)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079330
PubChem CID:	44556882
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002936] Cycloheptafurans

*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
NPO4034	Albizia adinocephala	Species	Fabaceae	Eukaryota	Stem bark and leaves	n.a.	n.a.	PMID[19299148]
NPO670	Hyrtios gumminae	Species	Thorectidae	Eukaryota	n.a.	Thai	n.a.	PMID[19788270]
NPO5186	Pimpinella aurea	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO670	Hyrtios gumminae	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4034	Albizia adinocephala	Species	Fabaceae	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	6

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	75000.0	nM	PMID[476782]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	125000.0	nM	PMID[476782]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	58000.0	nM	PMID[476782]
NPT396	Cell Line	T47D	Homo sapiens	IC50	=	70000.0	nM	PMID[476782]
NPT1396	Cell Line	NCI-H69	Homo sapiens	IC50	>	125000.0	nM	PMID[476782]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	90000.0	nM	PMID[476782]

☑ 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 NPC116639 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	381
0.1-0.2	1302
0.2-0.3	2696
0.3-0.4	5662
0.4-0.5	12008
0.5-0.6	8196
0.6-0.7	9040
0.7-0.8	3132
0.8-0.85	253
0.85-0.9	24
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9739	High Similarity	NPC261184
0.8926	High Similarity	NPC205765
0.8671	High Similarity	NPC472785
0.865	High Similarity	NPC472784
0.858	High Similarity	NPC472783
0.858	High Similarity	NPC472780
0.8562	High Similarity	NPC64568
0.8553	High Similarity	NPC75310
0.8519	High Similarity	NPC472781
0.8519	High Similarity	NPC472782
0.8509	High Similarity	NPC474611
0.8481	Intermediate Similarity	NPC472787
0.8476	Intermediate Similarity	NPC475779
0.8471	Intermediate Similarity	NPC472654
0.8466	Intermediate Similarity	NPC88841
0.8466	Intermediate Similarity	NPC288602
0.8457	Intermediate Similarity	NPC470789
0.8428	Intermediate Similarity	NPC246164
0.8428	Intermediate Similarity	NPC475777
0.8415	Intermediate Similarity	NPC123088
0.8405	Intermediate Similarity	NPC193798
0.8405	Intermediate Similarity	NPC5079
0.8405	Intermediate Similarity	NPC188649
0.8397	Intermediate Similarity	NPC97904
0.8395	Intermediate Similarity	NPC477403
0.8395	Intermediate Similarity	NPC472823
0.8395	Intermediate Similarity	NPC84349
0.8393	Intermediate Similarity	NPC471437
0.8375	Intermediate Similarity	NPC114880
0.8373	Intermediate Similarity	NPC296558
0.8355	Intermediate Similarity	NPC472376
0.8354	Intermediate Similarity	NPC224394
0.8354	Intermediate Similarity	NPC663
0.8354	Intermediate Similarity	NPC51568
0.8354	Intermediate Similarity	NPC234660
0.8354	Intermediate Similarity	NPC211625
0.8344	Intermediate Similarity	NPC335761
0.8344	Intermediate Similarity	NPC25255
0.8344	Intermediate Similarity	NPC250228
0.8344	Intermediate Similarity	NPC477402
0.8333	Intermediate Similarity	NPC194499
0.8333	Intermediate Similarity	NPC45101
0.8323	Intermediate Similarity	NPC243577
0.8323	Intermediate Similarity	NPC472786
0.8323	Intermediate Similarity	NPC44602
0.8323	Intermediate Similarity	NPC470995
0.8313	Intermediate Similarity	NPC473753
0.8313	Intermediate Similarity	NPC476853
0.8313	Intermediate Similarity	NPC478179
0.8313	Intermediate Similarity	NPC294511
0.8313	Intermediate Similarity	NPC476850
0.8313	Intermediate Similarity	NPC473766
0.8313	Intermediate Similarity	NPC476861
0.8313	Intermediate Similarity	NPC121615
0.8313	Intermediate Similarity	NPC472651
0.8303	Intermediate Similarity	NPC476858
0.8303	Intermediate Similarity	NPC476856
0.8303	Intermediate Similarity	NPC476857
0.8293	Intermediate Similarity	NPC18986
0.8293	Intermediate Similarity	NPC329938
0.8293	Intermediate Similarity	NPC82851
0.8293	Intermediate Similarity	NPC69028
0.8289	Intermediate Similarity	NPC473268
0.8282	Intermediate Similarity	NPC475967
0.8274	Intermediate Similarity	NPC285227
0.8274	Intermediate Similarity	NPC475641
0.8274	Intermediate Similarity	NPC159232
0.8274	Intermediate Similarity	NPC475237
0.8272	Intermediate Similarity	NPC469485
0.8267	Intermediate Similarity	NPC214097
0.8263	Intermediate Similarity	NPC472652
0.8258	Intermediate Similarity	NPC263337
0.8258	Intermediate Similarity	NPC473152
0.8253	Intermediate Similarity	NPC478178
0.8253	Intermediate Similarity	NPC121995
0.8253	Intermediate Similarity	NPC23387
0.8253	Intermediate Similarity	NPC149945
0.8253	Intermediate Similarity	NPC214600
0.8242	Intermediate Similarity	NPC134254
0.8242	Intermediate Similarity	NPC302369
0.8242	Intermediate Similarity	NPC39986
0.8242	Intermediate Similarity	NPC283209
0.8242	Intermediate Similarity	NPC477405
0.8239	Intermediate Similarity	NPC195325
0.8239	Intermediate Similarity	NPC470998
0.8232	Intermediate Similarity	NPC287559
0.8232	Intermediate Similarity	NPC472653
0.8224	Intermediate Similarity	NPC46896
0.8221	Intermediate Similarity	NPC261597
0.8221	Intermediate Similarity	NPC173544
0.8221	Intermediate Similarity	NPC304692
0.8221	Intermediate Similarity	NPC88007
0.8221	Intermediate Similarity	NPC249021
0.8221	Intermediate Similarity	NPC195954
0.8214	Intermediate Similarity	NPC302392
0.821	Intermediate Similarity	NPC281258
0.821	Intermediate Similarity	NPC35000
0.821	Intermediate Similarity	NPC214541
0.821	Intermediate Similarity	NPC44675
0.8205	Intermediate Similarity	NPC476946
0.8204	Intermediate Similarity	NPC472764
0.8204	Intermediate Similarity	NPC472775
0.8204	Intermediate Similarity	NPC472774
0.82	Intermediate Similarity	NPC473982
0.8199	Intermediate Similarity	NPC470996
0.8199	Intermediate Similarity	NPC44577
0.8199	Intermediate Similarity	NPC75906
0.8199	Intermediate Similarity	NPC33938
0.8193	Intermediate Similarity	NPC476860
0.8193	Intermediate Similarity	NPC470940
0.8193	Intermediate Similarity	NPC276551
0.8187	Intermediate Similarity	NPC196846
0.8187	Intermediate Similarity	NPC212257
0.8187	Intermediate Similarity	NPC156189
0.8187	Intermediate Similarity	NPC478177
0.8182	Intermediate Similarity	NPC263432
0.8182	Intermediate Similarity	NPC472771
0.8182	Intermediate Similarity	NPC472767
0.8182	Intermediate Similarity	NPC117986
0.8182	Intermediate Similarity	NPC68848
0.8176	Intermediate Similarity	NPC471632
0.8176	Intermediate Similarity	NPC236004
0.8171	Intermediate Similarity	NPC237155
0.8171	Intermediate Similarity	NPC473368
0.8171	Intermediate Similarity	NPC472779
0.8171	Intermediate Similarity	NPC475226
0.8165	Intermediate Similarity	NPC62799
0.816	Intermediate Similarity	NPC104736
0.816	Intermediate Similarity	NPC41880
0.816	Intermediate Similarity	NPC107646
0.816	Intermediate Similarity	NPC263265
0.816	Intermediate Similarity	NPC126723
0.816	Intermediate Similarity	NPC209364
0.8158	Intermediate Similarity	NPC158525
0.8155	Intermediate Similarity	NPC472765
0.8155	Intermediate Similarity	NPC271235
0.8155	Intermediate Similarity	NPC472766
0.8153	Intermediate Similarity	NPC84479
0.8153	Intermediate Similarity	NPC137295
0.8153	Intermediate Similarity	NPC476944
0.8148	Intermediate Similarity	NPC178932
0.8148	Intermediate Similarity	NPC30222
0.8144	Intermediate Similarity	NPC470875
0.8141	Intermediate Similarity	NPC62103
0.8141	Intermediate Similarity	NPC20578
0.8133	Intermediate Similarity	NPC472773
0.8133	Intermediate Similarity	NPC469338
0.8133	Intermediate Similarity	NPC285567
0.8133	Intermediate Similarity	NPC292389
0.8129	Intermediate Similarity	NPC67003
0.8129	Intermediate Similarity	NPC167340
0.8129	Intermediate Similarity	NPC90296
0.8129	Intermediate Similarity	NPC148374
0.8121	Intermediate Similarity	NPC191828
0.8118	Intermediate Similarity	NPC313717
0.8118	Intermediate Similarity	NPC315306
0.8113	Intermediate Similarity	NPC216755
0.8113	Intermediate Similarity	NPC71821
0.8113	Intermediate Similarity	NPC471174
0.811	Intermediate Similarity	NPC472776
0.811	Intermediate Similarity	NPC472283
0.811	Intermediate Similarity	NPC472772
0.811	Intermediate Similarity	NPC286722
0.811	Intermediate Similarity	NPC472777
0.811	Intermediate Similarity	NPC36655
0.811	Intermediate Similarity	NPC472778
0.8107	Intermediate Similarity	NPC118086
0.8107	Intermediate Similarity	NPC472659
0.8101	Intermediate Similarity	NPC5676
0.8098	Intermediate Similarity	NPC296807
0.8098	Intermediate Similarity	NPC155939
0.8098	Intermediate Similarity	NPC141538
0.8098	Intermediate Similarity	NPC469336
0.8098	Intermediate Similarity	NPC92979
0.8095	Intermediate Similarity	NPC270312
0.8095	Intermediate Similarity	NPC472282
0.8095	Intermediate Similarity	NPC476224
0.8092	Intermediate Similarity	NPC106247
0.8089	Intermediate Similarity	NPC205071
0.8089	Intermediate Similarity	NPC267632
0.8086	Intermediate Similarity	NPC471613
0.8086	Intermediate Similarity	NPC474219
0.8086	Intermediate Similarity	NPC474378
0.8086	Intermediate Similarity	NPC469503
0.8084	Intermediate Similarity	NPC469849
0.8084	Intermediate Similarity	NPC56358
0.8081	Intermediate Similarity	NPC472665
0.8075	Intermediate Similarity	NPC470997
0.8075	Intermediate Similarity	NPC46551
0.8075	Intermediate Similarity	NPC228842
0.8072	Intermediate Similarity	NPC470792
0.8072	Intermediate Similarity	NPC79571
0.8072	Intermediate Similarity	NPC6326
0.8072	Intermediate Similarity	NPC472668
0.8072	Intermediate Similarity	NPC96443
0.8072	Intermediate Similarity	NPC207978
0.8072	Intermediate Similarity	NPC197596
0.8072	Intermediate Similarity	NPC200782
0.8072	Intermediate Similarity	NPC290400
0.807	Intermediate Similarity	NPC94763

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 NPC116639 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	335
0.1-0.2	810
0.2-0.3	1654
0.3-0.4	2679
0.4-0.5	2227
0.5-0.6	1074
0.6-0.7	328
0.7-0.8	39
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8553	High Similarity	NPD5761	Phase 2
0.8553	High Similarity	NPD5760	Phase 2
0.8103	Intermediate Similarity	NPD8434	Phase 2
0.8023	Intermediate Similarity	NPD6764	Approved
0.8023	Intermediate Similarity	NPD6765	Approved
0.8012	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD6784	Approved
0.7841	Intermediate Similarity	NPD6785	Approved
0.7688	Intermediate Similarity	NPD4628	Phase 3
0.759	Intermediate Similarity	NPD6599	Discontinued
0.756	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7075	Discontinued
0.7471	Intermediate Similarity	NPD3882	Suspended
0.7396	Intermediate Similarity	NPD6801	Discontinued
0.7394	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1471	Phase 3
0.7391	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6799	Approved
0.7318	Intermediate Similarity	NPD6559	Discontinued
0.7299	Intermediate Similarity	NPD1247	Approved
0.7284	Intermediate Similarity	NPD2344	Approved
0.7278	Intermediate Similarity	NPD4380	Phase 2
0.7247	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6273	Approved
0.7241	Intermediate Similarity	NPD5494	Approved
0.7222	Intermediate Similarity	NPD2796	Approved
0.7209	Intermediate Similarity	NPD5402	Approved
0.7209	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5403	Approved
0.7202	Intermediate Similarity	NPD920	Approved
0.7195	Intermediate Similarity	NPD2800	Approved
0.7191	Intermediate Similarity	NPD7799	Discontinued
0.7186	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD919	Approved
0.7178	Intermediate Similarity	NPD5763	Approved
0.7178	Intermediate Similarity	NPD5762	Approved
0.7169	Intermediate Similarity	NPD7236	Approved
0.7158	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7819	Suspended
0.7151	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1549	Phase 2
0.7126	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6099	Approved
0.7117	Intermediate Similarity	NPD6100	Approved
0.7108	Intermediate Similarity	NPD2309	Approved
0.7102	Intermediate Similarity	NPD8127	Discontinued
0.7095	Intermediate Similarity	NPD3818	Discontinued
0.7093	Intermediate Similarity	NPD1934	Approved
0.7083	Intermediate Similarity	NPD5401	Approved
0.7081	Intermediate Similarity	NPD6355	Discontinued
0.7079	Intermediate Similarity	NPD6166	Phase 2
0.7079	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6002	Phase 3
0.7073	Intermediate Similarity	NPD6005	Phase 3
0.7073	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6004	Phase 3
0.7073	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2799	Discontinued
0.705	Intermediate Similarity	NPD8404	Phase 2
0.7037	Intermediate Similarity	NPD1607	Approved
0.7029	Intermediate Similarity	NPD3749	Approved
0.7022	Intermediate Similarity	NPD3926	Phase 2
0.7019	Intermediate Similarity	NPD1240	Approved
0.7018	Intermediate Similarity	NPD3226	Approved
0.7012	Intermediate Similarity	NPD1551	Phase 2
0.7011	Intermediate Similarity	NPD3817	Phase 2
0.7006	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2532	Approved
0.6982	Remote Similarity	NPD2534	Approved
0.6982	Remote Similarity	NPD2533	Approved
0.6974	Remote Similarity	NPD9092	Discovery
0.6962	Remote Similarity	NPD5647	Approved
0.6962	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5844	Phase 1
0.6959	Remote Similarity	NPD7239	Suspended
0.6957	Remote Similarity	NPD8312	Approved
0.6957	Remote Similarity	NPD8313	Approved
0.6954	Remote Similarity	NPD2801	Approved
0.6951	Remote Similarity	NPD1510	Phase 2
0.6951	Remote Similarity	NPD7033	Discontinued
0.6944	Remote Similarity	NPD7473	Discontinued
0.6943	Remote Similarity	NPD1876	Approved
0.694	Remote Similarity	NPD7251	Discontinued
0.6936	Remote Similarity	NPD7411	Suspended
0.6927	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3972	Approved
0.6919	Remote Similarity	NPD7458	Discontinued
0.691	Remote Similarity	NPD6959	Discontinued
0.6906	Remote Similarity	NPD3751	Discontinued
0.6902	Remote Similarity	NPD7808	Phase 3
0.6886	Remote Similarity	NPD1243	Approved
0.6885	Remote Similarity	NPD6797	Phase 2
0.6882	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD5735	Approved
0.6867	Remote Similarity	NPD2346	Discontinued
0.6845	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD8150	Discontinued
0.6842	Remote Similarity	NPD1512	Approved
0.6831	Remote Similarity	NPD7074	Phase 3
0.6821	Remote Similarity	NPD3057	Approved
0.6821	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7199	Phase 2
0.6815	Remote Similarity	NPD1608	Approved
0.6813	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.679	Remote Similarity	NPD2313	Discontinued
0.678	Remote Similarity	NPD7768	Phase 2
0.678	Remote Similarity	NPD4967	Phase 2
0.678	Remote Similarity	NPD4966	Approved
0.678	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4965	Approved
0.6778	Remote Similarity	NPD6232	Discontinued
0.6778	Remote Similarity	NPD3787	Discontinued
0.6776	Remote Similarity	NPD7054	Approved
0.677	Remote Similarity	NPD6832	Phase 2
0.6757	Remote Similarity	NPD7685	Pre-registration
0.6752	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.675	Remote Similarity	NPD2798	Approved
0.6748	Remote Similarity	NPD8032	Phase 2
0.6746	Remote Similarity	NPD3750	Approved
0.6739	Remote Similarity	NPD7472	Approved
0.6735	Remote Similarity	NPD3533	Approved
0.6735	Remote Similarity	NPD2972	Approved
0.6731	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6653	Approved
0.6727	Remote Similarity	NPD6651	Approved
0.6726	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD1511	Approved
0.672	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD4140	Approved
0.6707	Remote Similarity	NPD2935	Discontinued
0.6707	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD3887	Approved
0.6705	Remote Similarity	NPD37	Approved
0.6703	Remote Similarity	NPD2403	Approved
0.6703	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7435	Discontinued
0.6687	Remote Similarity	NPD3268	Approved
0.6687	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2797	Approved
0.6686	Remote Similarity	NPD7028	Phase 2
0.6685	Remote Similarity	NPD7315	Approved
0.6667	Remote Similarity	NPD7907	Approved
0.6667	Remote Similarity	NPD447	Suspended
0.665	Remote Similarity	NPD4111	Phase 1
0.665	Remote Similarity	NPD4665	Approved
0.6649	Remote Similarity	NPD8407	Phase 2
0.6647	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD4110	Phase 3
0.6647	Remote Similarity	NPD7003	Approved
0.6646	Remote Similarity	NPD6233	Phase 2
0.6633	Remote Similarity	NPD6777	Approved
0.6633	Remote Similarity	NPD6779	Approved
0.6633	Remote Similarity	NPD6778	Approved
0.6633	Remote Similarity	NPD6780	Approved
0.6633	Remote Similarity	NPD6776	Approved
0.6633	Remote Similarity	NPD6782	Approved
0.6633	Remote Similarity	NPD6781	Approved
0.663	Remote Similarity	NPD2163	Approved
0.6629	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD2296	Approved
0.6628	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5958	Discontinued
0.6627	Remote Similarity	NPD4534	Discontinued
0.6627	Remote Similarity	NPD2424	Discontinued
0.6627	Remote Similarity	NPD6353	Approved
0.6626	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD17	Approved
0.6616	Remote Similarity	NPD7696	Phase 3
0.6616	Remote Similarity	NPD7697	Approved
0.6616	Remote Similarity	NPD7698	Approved
0.6611	Remote Similarity	NPD6234	Discontinued
0.661	Remote Similarity	NPD6280	Approved
0.661	Remote Similarity	NPD6279	Approved
0.6608	Remote Similarity	NPD2354	Approved
0.6605	Remote Similarity	NPD9494	Approved
0.6604	Remote Similarity	NPD9717	Approved
0.6595	Remote Similarity	NPD7286	Phase 2
0.6592	Remote Similarity	NPD7057	Phase 3
0.6592	Remote Similarity	NPD7058	Phase 2
0.659	Remote Similarity	NPD4661	Approved
0.659	Remote Similarity	NPD4662	Approved
0.6585	Remote Similarity	NPD6798	Discontinued
0.6585	Remote Similarity	NPD3764	Approved
0.6585	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD1203	Approved
0.6583	Remote Similarity	NPD7871	Phase 2
0.6583	Remote Similarity	NPD7870	Phase 2
0.6582	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD8368	Discontinued

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