NPASS Compound

Structure

CID286422 OpenBabel06191716092D 44 48 0 0 1 0 0 0 0 0999 V2000 -6.9874 -2.3233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7282 -1.0401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2806 2.5663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2011 2.5663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2152 0.2745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7444 0.9192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0241 -2.3233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1758 1.6140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7075 1.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5057 -1.4679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2465 -1.0401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7649 -1.0401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4602 1.2831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2832 -1.0401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2011 0.8554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5424 -1.4679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4215 0.1891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0001 0.3756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8553 -1.3914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2761 -0.3467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9874 -1.4679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4602 2.1386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7937 0.4609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0241 -1.4679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8553 -0.7847 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8016 -1.0401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2011 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6005 -1.0401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5591 0.1276 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.6005 -1.0401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8016 -0.3467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2011 -1.3869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.3869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6005 -0.3467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8170 -0.2372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1447 0.8648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5905 0.1642 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6005 -0.3467 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5424 0.0810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2011 -2.2423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.2423 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5662 -0.4443 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 1.1031 0.8648 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 23 1 0 0 0 0 7 24 1 0 0 0 0 8 36 1 0 0 0 0 9 36 1 0 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 11 21 2 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 22 2 0 0 0 0 14 16 1 0 0 0 0 14 24 2 0 0 0 0 15 27 1 0 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 17 23 2 0 0 0 0 18 37 1 0 0 0 0 19 28 2 0 0 0 0 20 25 1 0 0 0 0 20 29 1 0 0 0 0 25 19 1 1 0 0 0 25 35 1 0 0 0 0 26 31 2 0 0 0 0 26 32 1 0 0 0 0 27 31 1 0 0 0 0 27 34 2 0 0 0 0 28 33 1 0 0 0 0 29 36 1 0 0 0 0 29 38 1 0 0 0 0 30 32 2 0 0 0 0 30 33 1 0 0 0 0 30 34 1 0 0 0 0 31 39 1 0 0 0 0 32 40 1 0 0 0 0 33 41 2 0 0 0 0 34 43 1 0 0 0 0 35 37 1 0 0 0 0 35 42 2 0 0 0 0 36 44 1 0 0 0 0 37 38 1 1 0 0 0 37 44 1 0 0 0 0 38 28 1 1 0 0 0 38 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	600.35
Volume:	649.398
LogP:	8.849
LogD:	5.124
LogS:	-3.88
# Rotatable Bonds:	9
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.278
Synthetic Accessibility Score:	6.387
Fsp3:	0.526
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:	-4.823
MDCK Permeability:	2.0692459656856954e-05
Pgp-inhibitor:	0.823
Pgp-substrate:	0.942
Human Intestinal Absorption (HIA):	0.459
20% Bioavailability (F20%):	0.937
30% Bioavailability (F30%):	0.09

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	93.49798583984375%
Volume Distribution (VD):	3.74
Pgp-substrate:	7.329866886138916%

ADMET: Metabolism

CYP1A2-inhibitor:	0.092
CYP1A2-substrate:	0.151
CYP2C19-inhibitor:	0.539
CYP2C19-substrate:	0.383
CYP2C9-inhibitor:	0.885
CYP2C9-substrate:	0.859
CYP2D6-inhibitor:	0.273
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.494
CYP3A4-substrate:	0.512

ADMET: Excretion

Clearance (CL):	11.863
Half-life (T1/2):	0.013

ADMET: Toxicity

hERG Blockers:	0.366
Human Hepatotoxicity (H-HT):	0.984
Drug-inuced Liver Injury (DILI):	0.261
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.98
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.237
Carcinogencity:	0.408
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC286422

Natural Product ID:	NPC286422
*Common Name:**	BYSLEZZCJZXNQG-OWATVDOJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BYSLEZZCJZXNQG-OWATVDOJSA-N
Standard InCHI:	InChI=1S/C38H48O6/c1-21(2)11-10-12-24(7)14-16-26-31(39)27(15-13-22(3)4)34-30(32(26)40)33(41)28-19-25-20-29-36(8,9)44-37(35(25)42,18-17-23(5)6)38(28,29)43-34/h11,13-14,17,19,25,29,39-40H,10,12,15-16,18,20H2,1-9H3/b24-14+/t25-,29?,37+,38-/m0/s1
SMILES:	CC(=CCC/C(=C/Cc1c(c(CC=C(C)C)c2c(c1O)C(=O)C1=C[C@H]3CC4C(C)(C)O[C@](CC=C(C)C)(C3=O)[C@]14O2)O)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3809214
PubChem CID:	16078252
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	latex	n.a.	PMID[17117343]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17117343]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	resin	n.a.	n.a.	PMID[19072548]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21486005]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	6.0	mm	PMID[525991]

☑ 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 NPC286422 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	444
0.1-0.2	1671
0.2-0.3	3283
0.3-0.4	7752
0.4-0.5	10802
0.5-0.6	5705
0.6-0.7	6284
0.7-0.8	6393
0.8-0.85	289
0.85-0.9	22
0.9-0.95	24
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
0.9805	High Similarity	NPC131578
0.9742	High Similarity	NPC189689
0.974	High Similarity	NPC94796
0.9679	High Similarity	NPC476255
0.9618	High Similarity	NPC223413
0.961	High Similarity	NPC475107
0.961	High Similarity	NPC43490
0.9557	High Similarity	NPC55422
0.9557	High Similarity	NPC47634
0.9557	High Similarity	NPC75141
0.9557	High Similarity	NPC476216
0.9554	High Similarity	NPC476056
0.9554	High Similarity	NPC62444
0.9494	High Similarity	NPC193222
0.9437	High Similarity	NPC476159
0.9437	High Similarity	NPC169018
0.9434	High Similarity	NPC158329
0.9434	High Similarity	NPC476146
0.9434	High Similarity	NPC40089
0.9434	High Similarity	NPC41598
0.9408	High Similarity	NPC476162
0.9379	High Similarity	NPC476139
0.9379	High Similarity	NPC476229
0.9313	High Similarity	NPC63514
0.9304	High Similarity	NPC476931
0.9264	High Similarity	NPC98943
0.9259	High Similarity	NPC476152
0.9259	High Similarity	NPC475080
0.9255	High Similarity	NPC476196
0.9207	High Similarity	NPC233978
0.9202	High Similarity	NPC162248
0.9141	High Similarity	NPC476311
0.9036	High Similarity	NPC473607
0.8976	High Similarity	NPC476199
0.8976	High Similarity	NPC476210
0.897	High Similarity	NPC475398
0.8963	High Similarity	NPC118128
0.8951	High Similarity	NPC475109
0.8938	High Similarity	NPC476929
0.8922	High Similarity	NPC473729
0.8916	High Similarity	NPC227275
0.8882	High Similarity	NPC475106
0.8868	High Similarity	NPC476930
0.875	High Similarity	NPC201127
0.8727	High Similarity	NPC102810
0.8696	High Similarity	NPC125969
0.8627	High Similarity	NPC469818
0.8623	High Similarity	NPC477529
0.8616	High Similarity	NPC470353
0.859	High Similarity	NPC82534
0.859	High Similarity	NPC473132
0.859	High Similarity	NPC470676
0.859	High Similarity	NPC473135
0.8589	High Similarity	NPC103816
0.8589	High Similarity	NPC61382
0.8571	High Similarity	NPC470352
0.8571	High Similarity	NPC469393
0.8571	High Similarity	NPC73899
0.8571	High Similarity	NPC17105
0.8571	High Similarity	NPC147363
0.8571	High Similarity	NPC474276
0.8563	High Similarity	NPC313717
0.8563	High Similarity	NPC315306
0.8545	High Similarity	NPC473908
0.8545	High Similarity	NPC316262
0.8545	High Similarity	NPC314653
0.8529	High Similarity	NPC5671
0.8528	High Similarity	NPC172687
0.8519	High Similarity	NPC161650
0.8519	High Similarity	NPC474637
0.8516	High Similarity	NPC204469
0.8506	High Similarity	NPC477272
0.8503	High Similarity	NPC54903
0.8503	High Similarity	NPC286074
0.85	High Similarity	NPC288534
0.8494	Intermediate Similarity	NPC17274
0.8494	Intermediate Similarity	NPC85047
0.8494	Intermediate Similarity	NPC120857
0.8491	Intermediate Similarity	NPC476509
0.8471	Intermediate Similarity	NPC329678
0.8466	Intermediate Similarity	NPC311574
0.8466	Intermediate Similarity	NPC264932
0.8462	Intermediate Similarity	NPC5990
0.8457	Intermediate Similarity	NPC470354
0.8457	Intermediate Similarity	NPC164427
0.8452	Intermediate Similarity	NPC111201
0.8447	Intermediate Similarity	NPC100134
0.8447	Intermediate Similarity	NPC209760
0.8443	Intermediate Similarity	NPC478059
0.8443	Intermediate Similarity	NPC470374
0.8443	Intermediate Similarity	NPC126204
0.8443	Intermediate Similarity	NPC478060
0.8443	Intermediate Similarity	NPC470377
0.8443	Intermediate Similarity	NPC292233
0.8443	Intermediate Similarity	NPC471975
0.8438	Intermediate Similarity	NPC305965
0.8421	Intermediate Similarity	NPC221820
0.8415	Intermediate Similarity	NPC313368
0.8412	Intermediate Similarity	NPC289244
0.8412	Intermediate Similarity	NPC245975
0.8408	Intermediate Similarity	NPC117716
0.8408	Intermediate Similarity	NPC470674
0.8408	Intermediate Similarity	NPC470673
0.8405	Intermediate Similarity	NPC210048
0.8397	Intermediate Similarity	NPC276565
0.8395	Intermediate Similarity	NPC476169
0.8393	Intermediate Similarity	NPC20734
0.8387	Intermediate Similarity	NPC82920
0.8387	Intermediate Similarity	NPC164697
0.8387	Intermediate Similarity	NPC289660
0.8385	Intermediate Similarity	NPC142527
0.8385	Intermediate Similarity	NPC210597
0.8385	Intermediate Similarity	NPC477957
0.8383	Intermediate Similarity	NPC469394
0.8377	Intermediate Similarity	NPC470671
0.8377	Intermediate Similarity	NPC474504
0.8377	Intermediate Similarity	NPC470672
0.8377	Intermediate Similarity	NPC474487
0.8375	Intermediate Similarity	NPC150928
0.8373	Intermediate Similarity	NPC472581
0.8373	Intermediate Similarity	NPC469395
0.8372	Intermediate Similarity	NPC476273
0.8354	Intermediate Similarity	NPC477955
0.8354	Intermediate Similarity	NPC474373
0.8353	Intermediate Similarity	NPC470942
0.8344	Intermediate Similarity	NPC18886
0.8343	Intermediate Similarity	NPC193698
0.8333	Intermediate Similarity	NPC236756
0.8333	Intermediate Similarity	NPC472799
0.8333	Intermediate Similarity	NPC311579
0.8333	Intermediate Similarity	NPC74397
0.8333	Intermediate Similarity	NPC150131
0.8333	Intermediate Similarity	NPC189130
0.8333	Intermediate Similarity	NPC214632
0.8323	Intermediate Similarity	NPC270913
0.8323	Intermediate Similarity	NPC472580
0.8323	Intermediate Similarity	NPC81474
0.8323	Intermediate Similarity	NPC471229
0.8314	Intermediate Similarity	NPC23553
0.8314	Intermediate Similarity	NPC77179
0.8313	Intermediate Similarity	NPC219861
0.8313	Intermediate Similarity	NPC473978
0.8313	Intermediate Similarity	NPC65775
0.8313	Intermediate Similarity	NPC10027
0.8303	Intermediate Similarity	NPC243701
0.8303	Intermediate Similarity	NPC470810
0.8303	Intermediate Similarity	NPC471973
0.8294	Intermediate Similarity	NPC91650
0.8293	Intermediate Similarity	NPC136674
0.8293	Intermediate Similarity	NPC474681
0.8293	Intermediate Similarity	NPC218313
0.8291	Intermediate Similarity	NPC472447
0.8291	Intermediate Similarity	NPC472446
0.8284	Intermediate Similarity	NPC152477
0.8282	Intermediate Similarity	NPC469934
0.8282	Intermediate Similarity	NPC275575
0.8282	Intermediate Similarity	NPC234485
0.8282	Intermediate Similarity	NPC471116
0.8282	Intermediate Similarity	NPC471456
0.828	Intermediate Similarity	NPC326193
0.828	Intermediate Similarity	NPC321148
0.828	Intermediate Similarity	NPC323884
0.828	Intermediate Similarity	NPC144499
0.828	Intermediate Similarity	NPC321629
0.8276	Intermediate Similarity	NPC246153
0.8276	Intermediate Similarity	NPC475656
0.8276	Intermediate Similarity	NPC8927
0.8276	Intermediate Similarity	NPC475148
0.8274	Intermediate Similarity	NPC235610
0.8272	Intermediate Similarity	NPC275878
0.8272	Intermediate Similarity	NPC45934
0.8272	Intermediate Similarity	NPC473996
0.8263	Intermediate Similarity	NPC109180
0.8263	Intermediate Similarity	NPC273959
0.8263	Intermediate Similarity	NPC159508
0.8263	Intermediate Similarity	NPC474240
0.8263	Intermediate Similarity	NPC475055
0.8261	Intermediate Similarity	NPC29777
0.8261	Intermediate Similarity	NPC471115
0.8261	Intermediate Similarity	NPC267117
0.8256	Intermediate Similarity	NPC156955
0.8256	Intermediate Similarity	NPC469345
0.8253	Intermediate Similarity	NPC478134
0.8253	Intermediate Similarity	NPC472346
0.8253	Intermediate Similarity	NPC117985
0.8253	Intermediate Similarity	NPC475883
0.8253	Intermediate Similarity	NPC474351
0.8253	Intermediate Similarity	NPC278427
0.8253	Intermediate Similarity	NPC234644
0.825	Intermediate Similarity	NPC296869
0.825	Intermediate Similarity	NPC39195
0.825	Intermediate Similarity	NPC145467
0.8246	Intermediate Similarity	NPC154986
0.8246	Intermediate Similarity	NPC30550
0.8246	Intermediate Similarity	NPC471969
0.8242	Intermediate Similarity	NPC204879
0.8239	Intermediate Similarity	NPC220418
0.8235	Intermediate Similarity	NPC28042
0.8235	Intermediate Similarity	NPC101107
0.8232	Intermediate Similarity	NPC6633

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 NPC286422 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	388
0.1-0.2	978
0.2-0.3	1880
0.3-0.4	2756
0.4-0.5	1976
0.5-0.6	780
0.6-0.7	288
0.7-0.8	104
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
0.8323	Intermediate Similarity	NPD2800	Approved
0.8282	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7075	Discontinued
0.8121	Intermediate Similarity	NPD3882	Suspended
0.811	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD2532	Approved
0.8063	Intermediate Similarity	NPD2534	Approved
0.8063	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD2533	Approved
0.8	Intermediate Similarity	NPD7819	Suspended
0.7976	Intermediate Similarity	NPD5494	Approved
0.7892	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD7411	Suspended
0.7861	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3749	Approved
0.7821	Intermediate Similarity	NPD6651	Approved
0.7818	Intermediate Similarity	NPD4380	Phase 2
0.7791	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7473	Discontinued
0.7725	Intermediate Similarity	NPD1934	Approved
0.7725	Intermediate Similarity	NPD6801	Discontinued
0.7719	Intermediate Similarity	NPD1247	Approved
0.7719	Intermediate Similarity	NPD6959	Discontinued
0.7711	Intermediate Similarity	NPD6599	Discontinued
0.7702	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1549	Phase 2
0.7688	Intermediate Similarity	NPD6166	Phase 2
0.7688	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD2403	Approved
0.7683	Intermediate Similarity	NPD1512	Approved
0.7679	Intermediate Similarity	NPD2801	Approved
0.7673	Intermediate Similarity	NPD6100	Approved
0.7673	Intermediate Similarity	NPD6099	Approved
0.7669	Intermediate Similarity	NPD6799	Approved
0.7625	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD8434	Phase 2
0.7602	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD3750	Approved
0.7588	Intermediate Similarity	NPD7768	Phase 2
0.7584	Intermediate Similarity	NPD7808	Phase 3
0.7578	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD5710	Approved
0.7572	Intermediate Similarity	NPD6232	Discontinued
0.7572	Intermediate Similarity	NPD5711	Approved
0.7561	Intermediate Similarity	NPD1511	Approved
0.7544	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3817	Phase 2
0.7528	Intermediate Similarity	NPD7251	Discontinued
0.75	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD1510	Phase 2
0.75	Intermediate Similarity	NPD919	Approved
0.7485	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1607	Approved
0.7472	Intermediate Similarity	NPD6797	Phase 2
0.7468	Intermediate Similarity	NPD1240	Approved
0.7458	Intermediate Similarity	NPD5844	Phase 1
0.7453	Intermediate Similarity	NPD2796	Approved
0.744	Intermediate Similarity	NPD3226	Approved
0.743	Intermediate Similarity	NPD6559	Discontinued
0.7429	Intermediate Similarity	NPD3926	Phase 2
0.7423	Intermediate Similarity	NPD1243	Approved
0.7418	Intermediate Similarity	NPD8150	Discontinued
0.7416	Intermediate Similarity	NPD7074	Phase 3
0.7407	Intermediate Similarity	NPD1471	Phase 3
0.7391	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1465	Phase 2
0.7363	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7054	Approved
0.7326	Intermediate Similarity	NPD5402	Approved
0.7321	Intermediate Similarity	NPD5403	Approved
0.7318	Intermediate Similarity	NPD7472	Approved
0.7317	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3751	Discontinued
0.7301	Intermediate Similarity	NPD2346	Discontinued
0.7301	Intermediate Similarity	NPD2344	Approved
0.7284	Intermediate Similarity	NPD3748	Approved
0.7284	Intermediate Similarity	NPD2799	Discontinued
0.7263	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD920	Approved
0.7202	Intermediate Similarity	NPD5401	Approved
0.7198	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD8312	Approved
0.7158	Intermediate Similarity	NPD8313	Approved
0.7151	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7390	Discontinued
0.7126	Intermediate Similarity	NPD2309	Approved
0.7115	Intermediate Similarity	NPD4749	Approved
0.7105	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5124	Phase 1
0.7099	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD3787	Discontinued
0.7073	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7698	Approved
0.7062	Intermediate Similarity	NPD7697	Approved
0.7062	Intermediate Similarity	NPD7435	Discontinued
0.7062	Intermediate Similarity	NPD7696	Phase 3
0.7059	Intermediate Similarity	NPD4287	Approved
0.7039	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD943	Approved
0.703	Intermediate Similarity	NPD1551	Phase 2
0.703	Intermediate Similarity	NPD2935	Discontinued
0.7026	Intermediate Similarity	NPD7871	Phase 2
0.7026	Intermediate Similarity	NPD7870	Phase 2
0.7019	Intermediate Similarity	NPD2313	Discontinued
0.7019	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD8366	Approved
0.701	Intermediate Similarity	NPD7907	Approved
0.6995	Remote Similarity	NPD6779	Approved
0.6995	Remote Similarity	NPD6778	Approved
0.6995	Remote Similarity	NPD6782	Approved
0.6995	Remote Similarity	NPD5953	Discontinued
0.6995	Remote Similarity	NPD6780	Approved
0.6995	Remote Similarity	NPD6777	Approved
0.6995	Remote Similarity	NPD6781	Approved
0.6995	Remote Similarity	NPD6776	Approved
0.6978	Remote Similarity	NPD7286	Phase 2
0.6971	Remote Similarity	NPD5760	Phase 2
0.6971	Remote Similarity	NPD5761	Phase 2
0.697	Remote Similarity	NPD8151	Discontinued
0.6964	Remote Similarity	NPD4628	Phase 3
0.6964	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4625	Phase 3
0.6936	Remote Similarity	NPD7458	Discontinued
0.6935	Remote Similarity	NPD7874	Approved
0.6935	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7228	Approved
0.6923	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7701	Phase 2
0.6914	Remote Similarity	NPD37	Approved
0.6914	Remote Similarity	NPD3268	Approved
0.6914	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.691	Remote Similarity	NPD6234	Discontinued
0.69	Remote Similarity	NPD7801	Approved
0.6894	Remote Similarity	NPD4908	Phase 1
0.6893	Remote Similarity	NPD4967	Phase 2
0.6893	Remote Similarity	NPD4965	Approved
0.6893	Remote Similarity	NPD4966	Approved
0.6891	Remote Similarity	NPD7699	Phase 2
0.6891	Remote Similarity	NPD7700	Phase 2
0.689	Remote Similarity	NPD447	Suspended
0.6889	Remote Similarity	NPD7229	Phase 3
0.6882	Remote Similarity	NPD3300	Phase 2
0.6875	Remote Similarity	NPD8491	Approved
0.6853	Remote Similarity	NPD8320	Phase 1
0.6853	Remote Similarity	NPD8319	Approved
0.6842	Remote Similarity	NPD8469	Approved
0.6839	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7199	Phase 2
0.6829	Remote Similarity	NPD4111	Phase 1
0.6829	Remote Similarity	NPD4665	Approved
0.6826	Remote Similarity	NPD5406	Approved
0.6826	Remote Similarity	NPD5408	Approved
0.6826	Remote Similarity	NPD5405	Approved
0.6826	Remote Similarity	NPD5404	Approved
0.6823	Remote Similarity	NPD6534	Approved
0.6823	Remote Similarity	NPD4360	Phase 2
0.6823	Remote Similarity	NPD4363	Phase 3
0.6823	Remote Similarity	NPD6535	Approved
0.681	Remote Similarity	NPD3764	Approved
0.6805	Remote Similarity	NPD2654	Approved
0.6802	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4361	Phase 2
0.6788	Remote Similarity	NPD230	Phase 1
0.6788	Remote Similarity	NPD6355	Discontinued
0.6774	Remote Similarity	NPD6765	Approved
0.6774	Remote Similarity	NPD6764	Approved
0.677	Remote Similarity	NPD2798	Approved
0.6769	Remote Similarity	NPD8285	Discontinued
0.6763	Remote Similarity	NPD5049	Phase 3
0.6751	Remote Similarity	NPD3057	Approved
0.6742	Remote Similarity	NPD4288	Approved
0.6733	Remote Similarity	NPD7783	Phase 2
0.6733	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.673	Remote Similarity	NPD9717	Approved
0.6728	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4060	Phase 1
0.6721	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD1203	Approved
0.6708	Remote Similarity	NPD1470	Approved
0.6707	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6585	Discontinued
0.67	Remote Similarity	NPD7584	Approved
0.6687	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3446	Phase 1
0.6684	Remote Similarity	NPD7685	Pre-registration
0.6667	Remote Similarity	NPD3533	Approved
0.6667	Remote Similarity	NPD7615	Clinical (unspecified phase)

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