NPASS Compound

Structure

NPC270958 OpenBabel07101718192D 42 46 0 0 1 0 0 0 0 0999 V2000 5.7633 5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1453 3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8363 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1369 -0.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5636 3.8305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 -0.4135 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 -0.8660 0.5000 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 1.5000 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 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1161 6.3564 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 4.7852 5.6132 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4762 4.6622 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 3.8581 2.7601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6369 0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5417 4.0385 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 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1369 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4980 4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1890 3.5032 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 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 1 0 0 0 0 0 0 0 0 0 4.4251 7.3074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6369 0.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8508 4.9895 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8289 5.1974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1369 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2109 3.2953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 18 2 0 0 0 0 5 21 1 0 0 0 0 6 22 1 0 0 0 0 7 31 1 0 0 0 0 9 10 2 0 0 0 0 9 23 1 0 0 0 0 11 12 1 0 0 0 0 11 31 1 0 0 0 0 12 33 1 0 0 0 0 13 24 1 0 0 0 0 13 26 1 0 0 0 0 14 25 1 0 0 0 0 14 32 1 0 0 0 0 15 17 1 0 0 0 0 15 35 1 0 0 0 0 16 33 1 0 0 0 0 16 34 1 0 0 0 0 17 1 1 6 0 0 0 17 18 1 0 0 0 0 18 29 1 0 0 0 0 19 3 1 6 0 0 0 19 23 1 0 0 0 0 19 27 1 0 0 0 0 20 4 1 1 0 0 0 20 28 1 0 0 0 0 20 30 1 0 0 0 0 21 36 2 0 0 0 0 21 41 1 0 0 0 0 22 37 2 0 0 0 0 22 42 1 0 0 0 0 23 38 2 0 0 0 0 24 27 1 0 0 0 0 24 39 1 1 0 0 0 25 28 1 0 0 0 0 25 41 1 1 0 0 0 26 32 1 6 0 0 0 26 33 1 0 0 0 0 27 34 1 1 0 0 0 28 31 1 1 0 0 0 29 40 2 0 0 0 0 30 29 1 1 0 0 0 30 42 1 0 0 0 0 31 32 1 1 0 0 0 32 8 1 6 0 0 0 33 34 1 6 0 0 0 34 10 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	584.33
Volume:	608.341
LogP:	2.968
LogD:	2.269
LogS:	-4.377
# Rotatable Bonds:	10
TPSA:	127.2
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.321
Synthetic Accessibility Score:	6.41
Fsp3:	0.765
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.445
MDCK Permeability:	2.8245463909115642e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.097
20% Bioavailability (F20%):	0.855
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.258
Plasma Protein Binding (PPB):	80.47171783447266%
Volume Distribution (VD):	1.02
Pgp-substrate:	15.148168563842773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.153
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.594
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.024
CYP3A4-inhibitor:	0.868
CYP3A4-substrate:	0.628

ADMET: Excretion

Clearance (CL):	2.285
Half-life (T1/2):	0.483

ADMET: Toxicity

hERG Blockers:	0.569
Human Hepatotoxicity (H-HT):	0.221
Drug-inuced Liver Injury (DILI):	0.424
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.947
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.573
Carcinogencity:	0.838
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC270958

Natural Product ID:	NPC270958
*Common Name:**	HEMHDIHNEPEXBX-CKVQJATHSA-N
IUPAC Name:	n.a.
Synonyms:	6Beta-Hydroxyneoboutomellerone
Standard InCHIKey:	HEMHDIHNEPEXBX-CKVQJATHSA-N
Standard InCHI:	InChI=1S/C34H48O8/c1-17(15-35)18(2)29(40)30(42-22(6)37)20(4)28-25(41-21(5)36)14-32(8)26-13-24(39)27-19(3)23(38)9-10-34(27)16-33(26,34)12-11-31(28,32)7/h9-10,17,19-20,24-28,30,35,39H,2,11-16H2,1,3-8H3/t17-,19+,20-,24+,25-,26-,27+,28-,30+,31+,32-,33-,34+/m0/s1
SMILES:	C[C@@H](CO)C(=C)C(=O)[C@@H]([C@@H](C)[C@H]1[C@H](C[C@@]2(C)[C@@H]3C[C@H]([C@H]4[C@H](C)C(=O)C=C[C@]54C[C@@]35CC[C@]12C)O)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1941156
PubChem CID:	57331959
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO16384	Neoboutonia melleri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22168134]
NPO16384	Neoboutonia melleri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22206869]
NPO16384	Neoboutonia melleri	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	2
Others	5

Activity Type	# Activity
Others	7

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	FC	=	31.0	n.a.	PMID[560250]
NPT2	Others	Unspecified	FC	=	5.1	n.a.	PMID[560250]
NPT2	Others	Unspecified	IC50	>	1000000.0	nM	PMID[560250]
NPT2	Others	Unspecified	FC	=	31.0	n.a.	PMID[560251]
NPT2	Others	Unspecified	FC	=	5.1	n.a.	PMID[560251]
NPT2	Others	Unspecified	FC	=	1.2	n.a.	PMID[560251]

☑ 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 NPC270958 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	239
0.1-0.2	1425
0.2-0.3	4862
0.3-0.4	8869
0.4-0.5	12030
0.5-0.6	6349
0.6-0.7	6075
0.7-0.8	2575
0.8-0.85	224
0.85-0.9	35
0.9-0.95	6
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9815	High Similarity	NPC118638
0.9811	High Similarity	NPC202889
0.9717	High Similarity	NPC170487
0.9717	High Similarity	NPC71348
0.9623	High Similarity	NPC118860
0.9623	High Similarity	NPC214797
0.9623	High Similarity	NPC231589
0.9434	High Similarity	NPC258543
0.9434	High Similarity	NPC241927
0.934	High Similarity	NPC470269
0.9167	High Similarity	NPC197428
0.9151	High Similarity	NPC181265
0.9083	High Similarity	NPC470281
0.9057	High Similarity	NPC235889
0.8981	High Similarity	NPC94529
0.8889	High Similarity	NPC44063
0.8879	High Similarity	NPC310586
0.8879	High Similarity	NPC29705
0.8868	High Similarity	NPC308351
0.8868	High Similarity	NPC271266
0.8829	High Similarity	NPC280782
0.8807	High Similarity	NPC211224
0.8796	High Similarity	NPC196528
0.8796	High Similarity	NPC278628
0.8796	High Similarity	NPC231530
0.8796	High Similarity	NPC475571
0.8761	High Similarity	NPC148458
0.875	High Similarity	NPC472926
0.875	High Similarity	NPC52634
0.8727	High Similarity	NPC304495
0.8727	High Similarity	NPC2766
0.8692	High Similarity	NPC15396
0.8684	High Similarity	NPC471854
0.8684	High Similarity	NPC239273
0.8684	High Similarity	NPC472927
0.8661	High Similarity	NPC100267
0.8661	High Similarity	NPC475524
0.8624	High Similarity	NPC470267
0.8611	High Similarity	NPC140723
0.8609	High Similarity	NPC311554
0.8609	High Similarity	NPC257457
0.8585	High Similarity	NPC114274
0.8584	High Similarity	NPC962
0.8571	High Similarity	NPC43775
0.8534	High Similarity	NPC473203
0.8534	High Similarity	NPC472933
0.8532	High Similarity	NPC96268
0.8519	High Similarity	NPC22388
0.8496	Intermediate Similarity	NPC264634
0.8491	Intermediate Similarity	NPC108078
0.8487	Intermediate Similarity	NPC473255
0.8482	Intermediate Similarity	NPC129689
0.8475	Intermediate Similarity	NPC222688
0.8462	Intermediate Similarity	NPC109973
0.8455	Intermediate Similarity	NPC265127
0.8455	Intermediate Similarity	NPC470309
0.844	Intermediate Similarity	NPC159442
0.8435	Intermediate Similarity	NPC266728
0.8435	Intermediate Similarity	NPC49492
0.8421	Intermediate Similarity	NPC250109
0.8421	Intermediate Similarity	NPC194100
0.8417	Intermediate Similarity	NPC15095
0.8411	Intermediate Similarity	NPC477854
0.8407	Intermediate Similarity	NPC115303
0.8393	Intermediate Similarity	NPC286174
0.8393	Intermediate Similarity	NPC77947
0.8378	Intermediate Similarity	NPC475294
0.8378	Intermediate Similarity	NPC144854
0.8378	Intermediate Similarity	NPC3316
0.8374	Intermediate Similarity	NPC471855
0.8364	Intermediate Similarity	NPC216245
0.8364	Intermediate Similarity	NPC470251
0.8364	Intermediate Similarity	NPC137657
0.8364	Intermediate Similarity	NPC2436
0.8364	Intermediate Similarity	NPC135854
0.8361	Intermediate Similarity	NPC470880
0.8349	Intermediate Similarity	NPC136289
0.8348	Intermediate Similarity	NPC473798
0.8347	Intermediate Similarity	NPC470882
0.8347	Intermediate Similarity	NPC473253
0.8347	Intermediate Similarity	NPC473265
0.8333	Intermediate Similarity	NPC472972
0.8333	Intermediate Similarity	NPC218383
0.8333	Intermediate Similarity	NPC147180
0.8333	Intermediate Similarity	NPC152117
0.8333	Intermediate Similarity	NPC221144
0.8333	Intermediate Similarity	NPC144956
0.8333	Intermediate Similarity	NPC234042
0.8333	Intermediate Similarity	NPC15390
0.8306	Intermediate Similarity	NPC469674
0.8306	Intermediate Similarity	NPC58029
0.8304	Intermediate Similarity	NPC154608
0.8304	Intermediate Similarity	NPC192813
0.8304	Intermediate Similarity	NPC277017
0.8302	Intermediate Similarity	NPC469599
0.8288	Intermediate Similarity	NPC96377
0.8288	Intermediate Similarity	NPC50535
0.8276	Intermediate Similarity	NPC251236
0.8276	Intermediate Similarity	NPC298278
0.8276	Intermediate Similarity	NPC40632
0.8276	Intermediate Similarity	NPC96312
0.8276	Intermediate Similarity	NPC328374
0.8273	Intermediate Similarity	NPC33973
0.8273	Intermediate Similarity	NPC70967
0.8273	Intermediate Similarity	NPC470310
0.8273	Intermediate Similarity	NPC275583
0.8264	Intermediate Similarity	NPC63186
0.8261	Intermediate Similarity	NPC472929
0.8257	Intermediate Similarity	NPC476223
0.8257	Intermediate Similarity	NPC224720
0.8257	Intermediate Similarity	NPC476240
0.8257	Intermediate Similarity	NPC81530
0.8246	Intermediate Similarity	NPC207689
0.8246	Intermediate Similarity	NPC472928
0.8235	Intermediate Similarity	NPC310511
0.8226	Intermediate Similarity	NPC34963
0.8224	Intermediate Similarity	NPC328162
0.8224	Intermediate Similarity	NPC200054
0.8224	Intermediate Similarity	NPC29410
0.8224	Intermediate Similarity	NPC477853
0.8224	Intermediate Similarity	NPC305483
0.8224	Intermediate Similarity	NPC173272
0.8224	Intermediate Similarity	NPC96859
0.8224	Intermediate Similarity	NPC42042
0.822	Intermediate Similarity	NPC476960
0.822	Intermediate Similarity	NPC475041
0.8214	Intermediate Similarity	NPC220974
0.8214	Intermediate Similarity	NPC201908
0.8214	Intermediate Similarity	NPC176949
0.8214	Intermediate Similarity	NPC251824
0.8214	Intermediate Similarity	NPC86852
0.8214	Intermediate Similarity	NPC472925
0.8211	Intermediate Similarity	NPC35109
0.8211	Intermediate Similarity	NPC221414
0.8211	Intermediate Similarity	NPC471407
0.8208	Intermediate Similarity	NPC196485
0.8208	Intermediate Similarity	NPC245972
0.8208	Intermediate Similarity	NPC111015
0.8205	Intermediate Similarity	NPC472934
0.8205	Intermediate Similarity	NPC153651
0.8198	Intermediate Similarity	NPC47281
0.8198	Intermediate Similarity	NPC255309
0.8198	Intermediate Similarity	NPC28656
0.819	Intermediate Similarity	NPC474906
0.819	Intermediate Similarity	NPC18547
0.819	Intermediate Similarity	NPC471398
0.8182	Intermediate Similarity	NPC477054
0.8182	Intermediate Similarity	NPC53222
0.8167	Intermediate Similarity	NPC269642
0.8167	Intermediate Similarity	NPC65858
0.8165	Intermediate Similarity	NPC476274
0.816	Intermediate Similarity	NPC469673
0.8158	Intermediate Similarity	NPC76084
0.8158	Intermediate Similarity	NPC5284
0.8158	Intermediate Similarity	NPC6206
0.8158	Intermediate Similarity	NPC163314
0.8151	Intermediate Similarity	NPC471406
0.8151	Intermediate Similarity	NPC19336
0.8151	Intermediate Similarity	NPC185876
0.8151	Intermediate Similarity	NPC241192
0.8148	Intermediate Similarity	NPC190554
0.8148	Intermediate Similarity	NPC18509
0.8145	Intermediate Similarity	NPC279478
0.8145	Intermediate Similarity	NPC196921
0.8145	Intermediate Similarity	NPC241935
0.8145	Intermediate Similarity	NPC220757
0.8142	Intermediate Similarity	NPC469844
0.8142	Intermediate Similarity	NPC295244
0.8142	Intermediate Similarity	NPC293850
0.8142	Intermediate Similarity	NPC275539
0.8142	Intermediate Similarity	NPC189075
0.8136	Intermediate Similarity	NPC21326
0.8131	Intermediate Similarity	NPC470016
0.8131	Intermediate Similarity	NPC184848
0.8131	Intermediate Similarity	NPC98639
0.8131	Intermediate Similarity	NPC317586
0.8131	Intermediate Similarity	NPC69548
0.8131	Intermediate Similarity	NPC48330
0.8125	Intermediate Similarity	NPC257353
0.8125	Intermediate Similarity	NPC102352
0.8125	Intermediate Similarity	NPC28791
0.812	Intermediate Similarity	NPC152199
0.812	Intermediate Similarity	NPC190286
0.812	Intermediate Similarity	NPC134869
0.812	Intermediate Similarity	NPC235539
0.8115	Intermediate Similarity	NPC47113
0.8115	Intermediate Similarity	NPC473635
0.8115	Intermediate Similarity	NPC174367
0.8113	Intermediate Similarity	NPC470376
0.8113	Intermediate Similarity	NPC477855
0.8113	Intermediate Similarity	NPC470375
0.8113	Intermediate Similarity	NPC109414
0.8108	Intermediate Similarity	NPC264048
0.8108	Intermediate Similarity	NPC191892
0.8108	Intermediate Similarity	NPC311612
0.8108	Intermediate Similarity	NPC87927
0.8108	Intermediate Similarity	NPC95585
0.8108	Intermediate Similarity	NPC312900
0.8108	Intermediate Similarity	NPC282233
0.8108	Intermediate Similarity	NPC469985

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 NPC270958 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	1638
0.2-0.3	3904
0.3-0.4	2229
0.4-0.5	672
0.5-0.6	224
0.6-0.7	128
0.7-0.8	94
0.8-0.85	32
0.85-0.9	30
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9083	High Similarity	NPD6650	Approved
0.9083	High Similarity	NPD6649	Approved
0.9	High Similarity	NPD8297	Approved
0.8981	High Similarity	NPD6881	Approved
0.8981	High Similarity	NPD6899	Approved
0.8909	High Similarity	NPD8130	Phase 1
0.8899	High Similarity	NPD6372	Approved
0.8899	High Similarity	NPD6373	Approved
0.8889	High Similarity	NPD5697	Approved
0.8829	High Similarity	NPD6882	Approved
0.8818	High Similarity	NPD6883	Approved
0.8818	High Similarity	NPD7102	Approved
0.8818	High Similarity	NPD7290	Approved
0.8807	High Similarity	NPD6011	Approved
0.8796	High Similarity	NPD6675	Approved
0.8796	High Similarity	NPD6402	Approved
0.8796	High Similarity	NPD5739	Approved
0.8796	High Similarity	NPD7128	Approved
0.8739	High Similarity	NPD6869	Approved
0.8739	High Similarity	NPD6847	Approved
0.8739	High Similarity	NPD6617	Approved
0.8727	High Similarity	NPD6012	Approved
0.8727	High Similarity	NPD6013	Approved
0.8727	High Similarity	NPD6014	Approved
0.8718	High Similarity	NPD7604	Phase 2
0.8636	High Similarity	NPD7320	Approved
0.8621	High Similarity	NPD6319	Approved
0.8584	High Similarity	NPD4632	Approved
0.8545	High Similarity	NPD5701	Approved
0.8522	High Similarity	NPD6009	Approved
0.8455	Intermediate Similarity	NPD6008	Approved
0.8407	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.839	Intermediate Similarity	NPD5983	Phase 2
0.8333	Intermediate Similarity	NPD5285	Approved
0.8333	Intermediate Similarity	NPD5286	Approved
0.8333	Intermediate Similarity	NPD7492	Approved
0.8333	Intermediate Similarity	NPD4696	Approved
0.8305	Intermediate Similarity	NPD6054	Approved
0.8291	Intermediate Similarity	NPD6335	Approved
0.8279	Intermediate Similarity	NPD7736	Approved
0.8264	Intermediate Similarity	NPD6616	Approved
0.8264	Intermediate Similarity	NPD6336	Discontinued
0.8257	Intermediate Similarity	NPD5223	Approved
0.822	Intermediate Similarity	NPD7101	Approved
0.822	Intermediate Similarity	NPD7100	Approved
0.8205	Intermediate Similarity	NPD6317	Approved
0.8197	Intermediate Similarity	NPD7078	Approved
0.8182	Intermediate Similarity	NPD5226	Approved
0.8182	Intermediate Similarity	NPD4633	Approved
0.8182	Intermediate Similarity	NPD5211	Phase 2
0.8182	Intermediate Similarity	NPD5225	Approved
0.8182	Intermediate Similarity	NPD5224	Approved
0.8167	Intermediate Similarity	NPD6370	Approved
0.8148	Intermediate Similarity	NPD6083	Phase 2
0.8148	Intermediate Similarity	NPD4755	Approved
0.8148	Intermediate Similarity	NPD6084	Phase 2
0.8136	Intermediate Similarity	NPD6314	Approved
0.8136	Intermediate Similarity	NPD6313	Approved
0.812	Intermediate Similarity	NPD6274	Approved
0.8108	Intermediate Similarity	NPD5174	Approved
0.8108	Intermediate Similarity	NPD5175	Approved
0.8083	Intermediate Similarity	NPD6016	Approved
0.8083	Intermediate Similarity	NPD6015	Approved
0.8056	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD5221	Approved
0.8056	Intermediate Similarity	NPD5222	Approved
0.8049	Intermediate Similarity	NPD8293	Discontinued
0.8036	Intermediate Similarity	NPD5141	Approved
0.8019	Intermediate Similarity	NPD6079	Approved
0.8017	Intermediate Similarity	NPD5988	Approved
0.8	Intermediate Similarity	NPD6059	Approved
0.8	Intermediate Similarity	NPD4700	Approved
0.8	Intermediate Similarity	NPD4634	Approved
0.7982	Intermediate Similarity	NPD5173	Approved
0.7982	Intermediate Similarity	NPD4729	Approved
0.7982	Intermediate Similarity	NPD4730	Approved
0.7966	Intermediate Similarity	NPD6868	Approved
0.7944	Intermediate Similarity	NPD6399	Phase 3
0.7934	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7909	Intermediate Similarity	NPD5696	Approved
0.789	Intermediate Similarity	NPD4697	Phase 3
0.7845	Intermediate Similarity	NPD5249	Phase 3
0.7845	Intermediate Similarity	NPD5250	Approved
0.7845	Intermediate Similarity	NPD5251	Approved
0.7845	Intermediate Similarity	NPD5248	Approved
0.7845	Intermediate Similarity	NPD5247	Approved
0.783	Intermediate Similarity	NPD5328	Approved
0.7807	Intermediate Similarity	NPD4767	Approved
0.7807	Intermediate Similarity	NPD4768	Approved
0.7798	Intermediate Similarity	NPD5695	Phase 3
0.7798	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD4754	Approved
0.7787	Intermediate Similarity	NPD6909	Approved
0.7787	Intermediate Similarity	NPD6908	Approved
0.7748	Intermediate Similarity	NPD7638	Approved
0.7736	Intermediate Similarity	NPD6672	Approved
0.7736	Intermediate Similarity	NPD5737	Approved
0.7692	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5135	Approved
0.7692	Intermediate Similarity	NPD5169	Approved
0.7679	Intermediate Similarity	NPD7640	Approved
0.7679	Intermediate Similarity	NPD7639	Approved
0.7672	Intermediate Similarity	NPD5128	Approved
0.7664	Intermediate Similarity	NPD6673	Approved
0.7664	Intermediate Similarity	NPD6080	Approved
0.7664	Intermediate Similarity	NPD6904	Approved
0.7661	Intermediate Similarity	NPD8328	Phase 3
0.7658	Intermediate Similarity	NPD7902	Approved
0.7636	Intermediate Similarity	NPD5210	Approved
0.7636	Intermediate Similarity	NPD4629	Approved
0.7627	Intermediate Similarity	NPD5216	Approved
0.7627	Intermediate Similarity	NPD5217	Approved
0.7627	Intermediate Similarity	NPD5127	Approved
0.7627	Intermediate Similarity	NPD5215	Approved
0.7615	Intermediate Similarity	NPD4202	Approved
0.7603	Intermediate Similarity	NPD7115	Discovery
0.7559	Intermediate Similarity	NPD6033	Approved
0.7547	Intermediate Similarity	NPD7334	Approved
0.7547	Intermediate Similarity	NPD7521	Approved
0.7547	Intermediate Similarity	NPD5330	Approved
0.7547	Intermediate Similarity	NPD3618	Phase 1
0.7547	Intermediate Similarity	NPD6684	Approved
0.7547	Intermediate Similarity	NPD6409	Approved
0.7547	Intermediate Similarity	NPD7146	Approved
0.7545	Intermediate Similarity	NPD7748	Approved
0.75	Intermediate Similarity	NPD4753	Phase 2
0.7444	Intermediate Similarity	NPD6333	Approved
0.7444	Intermediate Similarity	NPD6334	Approved
0.7438	Intermediate Similarity	NPD5167	Approved
0.7436	Intermediate Similarity	NPD6412	Phase 2
0.7407	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6903	Approved
0.7402	Intermediate Similarity	NPD7507	Approved
0.7387	Intermediate Similarity	NPD7900	Approved
0.7387	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD6001	Approved
0.7383	Intermediate Similarity	NPD6098	Approved
0.7373	Intermediate Similarity	NPD5168	Approved
0.7364	Intermediate Similarity	NPD5284	Approved
0.7364	Intermediate Similarity	NPD5694	Approved
0.7364	Intermediate Similarity	NPD6050	Approved
0.7364	Intermediate Similarity	NPD5281	Approved
0.7364	Intermediate Similarity	NPD7515	Phase 2
0.7364	Intermediate Similarity	NPD8034	Phase 2
0.7364	Intermediate Similarity	NPD5693	Phase 1
0.7364	Intermediate Similarity	NPD8035	Phase 2
0.7358	Intermediate Similarity	NPD3666	Approved
0.7358	Intermediate Similarity	NPD3665	Phase 1
0.7358	Intermediate Similarity	NPD4786	Approved
0.7358	Intermediate Similarity	NPD3133	Approved
0.7317	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5329	Approved
0.7273	Intermediate Similarity	NPD6053	Discontinued
0.7273	Intermediate Similarity	NPD5692	Phase 3
0.7231	Intermediate Similarity	NPD7319	Approved
0.7222	Intermediate Similarity	NPD5690	Phase 2
0.7196	Intermediate Similarity	NPD4197	Approved
0.717	Intermediate Similarity	NPD3667	Approved
0.7156	Intermediate Similarity	NPD3573	Approved
0.7143	Intermediate Similarity	NPD6614	Approved
0.7121	Intermediate Similarity	NPD7260	Phase 2
0.7094	Intermediate Similarity	NPD7632	Discontinued
0.7083	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD5279	Phase 3
0.7064	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5959	Approved
0.7025	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD4223	Phase 3
0.7009	Intermediate Similarity	NPD4221	Approved
0.6977	Remote Similarity	NPD6067	Discontinued
0.6972	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5207	Approved
0.6953	Remote Similarity	NPD8033	Approved
0.6953	Remote Similarity	NPD7503	Approved
0.6942	Remote Similarity	NPD6686	Approved
0.6937	Remote Similarity	NPD5208	Approved
0.6917	Remote Similarity	NPD5956	Approved
0.6909	Remote Similarity	NPD4694	Approved
0.6909	Remote Similarity	NPD5280	Approved
0.6903	Remote Similarity	NPD6411	Approved
0.6885	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8294	Approved
0.6875	Remote Similarity	NPD8377	Approved
0.687	Remote Similarity	NPD5654	Approved
0.6852	Remote Similarity	NPD6435	Approved
0.685	Remote Similarity	NPD7328	Approved
0.685	Remote Similarity	NPD7327	Approved
0.6829	Remote Similarity	NPD6371	Approved
0.6822	Remote Similarity	NPD8335	Approved
0.6822	Remote Similarity	NPD8296	Approved
0.6822	Remote Similarity	NPD8380	Approved
0.6822	Remote Similarity	NPD8378	Approved
0.6822	Remote Similarity	NPD8379	Approved
0.6822	Remote Similarity	NPD4695	Discontinued
0.6814	Remote Similarity	NPD5785	Approved
0.6807	Remote Similarity	NPD5091	Approved
0.6806	Remote Similarity	NPD7236	Approved
0.6797	Remote Similarity	NPD4522	Approved
0.6797	Remote Similarity	NPD7516	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