NPASS Compound

Structure

NPC71348 OpenBabel07101718192D 39 43 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 6.6369 0.1340 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 -1.7321 -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 5.1369 -0.7321 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 2.2109 3.2953 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 17 2 0 0 0 0 5 20 1 0 0 0 0 6 29 1 0 0 0 0 8 9 2 0 0 0 0 8 21 1 0 0 0 0 10 11 1 0 0 0 0 10 29 1 0 0 0 0 11 31 1 0 0 0 0 12 22 1 0 0 0 0 12 24 1 0 0 0 0 13 23 1 0 0 0 0 13 30 1 0 0 0 0 14 16 1 0 0 0 0 14 33 1 0 0 0 0 15 31 1 0 0 0 0 15 32 1 0 0 0 0 16 1 1 6 0 0 0 16 17 1 0 0 0 0 17 27 1 0 0 0 0 18 3 1 6 0 0 0 18 21 1 0 0 0 0 18 25 1 0 0 0 0 19 4 1 1 0 0 0 19 26 1 0 0 0 0 19 28 1 0 0 0 0 20 34 2 0 0 0 0 20 39 1 0 0 0 0 21 35 2 0 0 0 0 22 25 1 0 0 0 0 22 36 1 1 0 0 0 23 26 1 0 0 0 0 23 39 1 1 0 0 0 24 30 1 6 0 0 0 24 31 1 0 0 0 0 25 32 1 1 0 0 0 26 29 1 1 0 0 0 27 28 1 0 0 0 0 27 37 2 0 0 0 0 28 38 1 1 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 31 32 1 6 0 0 0 32 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	542.32
Volume:	567.595
LogP:	2.743
LogD:	2.356
LogS:	-4.452
# Rotatable Bonds:	8
TPSA:	117.97
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.37
Synthetic Accessibility Score:	6.362
Fsp3:	0.812
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.339
MDCK Permeability:	2.5581728550605476e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.054
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.087
30% Bioavailability (F30%):	0.216

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.539
Plasma Protein Binding (PPB):	92.49241638183594%
Volume Distribution (VD):	0.653
Pgp-substrate:	5.58406400680542%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.486
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.779
CYP2C9-inhibitor:	0.022
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.93
CYP3A4-substrate:	0.796

ADMET: Excretion

Clearance (CL):	3.66
Half-life (T1/2):	0.277

ADMET: Toxicity

hERG Blockers:	0.194
Human Hepatotoxicity (H-HT):	0.291
Drug-inuced Liver Injury (DILI):	0.224
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.878
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.155
Carcinogencity:	0.874
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC71348

Natural Product ID:	NPC71348
*Common Name:**	BSGPJBALTHTFJC-AOONZWGDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BSGPJBALTHTFJC-AOONZWGDSA-N
Standard InCHI:	InChI=1S/C32H46O7/c1-16(14-33)17(2)27(37)28(38)19(4)26-23(39-20(5)34)13-30(7)24-12-22(36)25-18(3)21(35)8-9-32(25)15-31(24,32)11-10-29(26,30)6/h8-9,16,18-19,22-26,28,33,36,38H,2,10-15H2,1,3-7H3/t16-,18+,19-,22+,23-,24-,25+,26-,28+,29+,30-,31-,32+/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)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1941157
PubChem CID:	57331960
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	4

Activity Type	# Activity
Others	6

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	FC	=	35.0	n.a.	PMID[549608]
NPT2	Others	Unspecified	FC	=	1.1	n.a.	PMID[549608]
NPT2	Others	Unspecified	IC50	>	1000000.0	nM	PMID[549608]
NPT2	Others	Unspecified	FC	=	35.0	n.a.	PMID[549609]
NPT2	Others	Unspecified	FC	=	1.1	n.a.	PMID[549609]

☑ 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 NPC71348 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	224
0.1-0.2	1347
0.2-0.3	4771
0.3-0.4	9098
0.4-0.5	11979
0.5-0.6	6252
0.6-0.7	6130
0.7-0.8	2561
0.8-0.85	274
0.85-0.9	47
0.9-0.95	6
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9717	High Similarity	NPC270958
0.9709	High Similarity	NPC241927
0.9709	High Similarity	NPC258543
0.9537	High Similarity	NPC118638
0.9528	High Similarity	NPC202889
0.9524	High Similarity	NPC214797
0.9524	High Similarity	NPC231589
0.9524	High Similarity	NPC118860
0.9434	High Similarity	NPC170487
0.9417	High Similarity	NPC181265
0.932	High Similarity	NPC235889
0.9245	High Similarity	NPC197428
0.9057	High Similarity	NPC470269
0.9057	High Similarity	NPC211224
0.9057	High Similarity	NPC94529
0.8962	High Similarity	NPC44063
0.8952	High Similarity	NPC29705
0.8942	High Similarity	NPC308351
0.8942	High Similarity	NPC271266
0.8942	High Similarity	NPC15396
0.8868	High Similarity	NPC278628
0.8868	High Similarity	NPC231530
0.8835	High Similarity	NPC114274
0.8829	High Similarity	NPC148458
0.8807	High Similarity	NPC470281
0.8796	High Similarity	NPC2766
0.8774	High Similarity	NPC310586
0.875	High Similarity	NPC471854
0.875	High Similarity	NPC239273
0.8738	High Similarity	NPC108078
0.8727	High Similarity	NPC100267
0.8727	High Similarity	NPC475524
0.8727	High Similarity	NPC280782
0.8692	High Similarity	NPC196528
0.8692	High Similarity	NPC470267
0.8692	High Similarity	NPC265127
0.8679	High Similarity	NPC140723
0.8673	High Similarity	NPC257457
0.8673	High Similarity	NPC311554
0.8654	High Similarity	NPC477854
0.8649	High Similarity	NPC52634
0.8636	High Similarity	NPC43775
0.8624	High Similarity	NPC304495
0.8611	High Similarity	NPC475294
0.8598	High Similarity	NPC96268
0.8585	High Similarity	NPC22388
0.8585	High Similarity	NPC136289
0.8571	High Similarity	NPC144956
0.8571	High Similarity	NPC15390
0.8544	High Similarity	NPC469599
0.8519	High Similarity	NPC475571
0.8519	High Similarity	NPC470309
0.8505	High Similarity	NPC470310
0.8505	High Similarity	NPC159442
0.8491	Intermediate Similarity	NPC224720
0.8491	Intermediate Similarity	NPC476240
0.8491	Intermediate Similarity	NPC476223
0.8491	Intermediate Similarity	NPC81530
0.8482	Intermediate Similarity	NPC472926
0.8482	Intermediate Similarity	NPC194100
0.8482	Intermediate Similarity	NPC250109
0.8482	Intermediate Similarity	NPC962
0.8462	Intermediate Similarity	NPC477853
0.8462	Intermediate Similarity	NPC96859
0.8462	Intermediate Similarity	NPC328162
0.8462	Intermediate Similarity	NPC173272
0.8462	Intermediate Similarity	NPC305483
0.8447	Intermediate Similarity	NPC245972
0.8447	Intermediate Similarity	NPC196485
0.8447	Intermediate Similarity	NPC111015
0.844	Intermediate Similarity	NPC220974
0.844	Intermediate Similarity	NPC472925
0.844	Intermediate Similarity	NPC3316
0.844	Intermediate Similarity	NPC144854
0.8435	Intermediate Similarity	NPC473203
0.8426	Intermediate Similarity	NPC255309
0.8426	Intermediate Similarity	NPC28656
0.8426	Intermediate Similarity	NPC137657
0.8421	Intermediate Similarity	NPC472927
0.8411	Intermediate Similarity	NPC477054
0.8403	Intermediate Similarity	NPC473253
0.8396	Intermediate Similarity	NPC218383
0.8396	Intermediate Similarity	NPC476274
0.8393	Intermediate Similarity	NPC221144
0.8393	Intermediate Similarity	NPC152117
0.8393	Intermediate Similarity	NPC264634
0.8393	Intermediate Similarity	NPC234042
0.839	Intermediate Similarity	NPC473255
0.8381	Intermediate Similarity	NPC190554
0.8381	Intermediate Similarity	NPC18509
0.8378	Intermediate Similarity	NPC5284
0.8378	Intermediate Similarity	NPC6206
0.8376	Intermediate Similarity	NPC222688
0.8365	Intermediate Similarity	NPC470016
0.8365	Intermediate Similarity	NPC98639
0.8365	Intermediate Similarity	NPC69548
0.8365	Intermediate Similarity	NPC184848
0.8365	Intermediate Similarity	NPC317586
0.8365	Intermediate Similarity	NPC48330
0.8364	Intermediate Similarity	NPC469844
0.8364	Intermediate Similarity	NPC154608
0.8364	Intermediate Similarity	NPC192813
0.8364	Intermediate Similarity	NPC277017
0.8362	Intermediate Similarity	NPC109973
0.835	Intermediate Similarity	NPC477855
0.835	Intermediate Similarity	NPC470375
0.835	Intermediate Similarity	NPC109414
0.835	Intermediate Similarity	NPC470376
0.8349	Intermediate Similarity	NPC96377
0.8349	Intermediate Similarity	NPC257353
0.8333	Intermediate Similarity	NPC264048
0.8333	Intermediate Similarity	NPC298278
0.8333	Intermediate Similarity	NPC311612
0.8333	Intermediate Similarity	NPC191892
0.8333	Intermediate Similarity	NPC266728
0.8333	Intermediate Similarity	NPC49492
0.8333	Intermediate Similarity	NPC236390
0.8333	Intermediate Similarity	NPC55872
0.8333	Intermediate Similarity	NPC312900
0.8333	Intermediate Similarity	NPC275583
0.8319	Intermediate Similarity	NPC255017
0.8319	Intermediate Similarity	NPC15095
0.8318	Intermediate Similarity	NPC477052
0.8318	Intermediate Similarity	NPC477051
0.8318	Intermediate Similarity	NPC477053
0.8304	Intermediate Similarity	NPC472928
0.8302	Intermediate Similarity	NPC176845
0.8302	Intermediate Similarity	NPC477813
0.8288	Intermediate Similarity	NPC214644
0.8288	Intermediate Similarity	NPC10064
0.8288	Intermediate Similarity	NPC41405
0.8288	Intermediate Similarity	NPC170221
0.8286	Intermediate Similarity	NPC95565
0.8286	Intermediate Similarity	NPC29410
0.8286	Intermediate Similarity	NPC200054
0.8286	Intermediate Similarity	NPC49371
0.8286	Intermediate Similarity	NPC42042
0.8279	Intermediate Similarity	NPC471855
0.8276	Intermediate Similarity	NPC61520
0.8276	Intermediate Similarity	NPC472933
0.8276	Intermediate Similarity	NPC476960
0.8276	Intermediate Similarity	NPC475041
0.8273	Intermediate Similarity	NPC185
0.8273	Intermediate Similarity	NPC220229
0.8273	Intermediate Similarity	NPC475060
0.8269	Intermediate Similarity	NPC166906
0.8264	Intermediate Similarity	NPC470880
0.8257	Intermediate Similarity	NPC72255
0.8257	Intermediate Similarity	NPC135854
0.8257	Intermediate Similarity	NPC470251
0.8257	Intermediate Similarity	NPC477812
0.8257	Intermediate Similarity	NPC216245
0.8257	Intermediate Similarity	NPC2436
0.8252	Intermediate Similarity	NPC185936
0.8252	Intermediate Similarity	NPC168027
0.8252	Intermediate Similarity	NPC154101
0.825	Intermediate Similarity	NPC470882
0.825	Intermediate Similarity	NPC473265
0.8246	Intermediate Similarity	NPC471398
0.8241	Intermediate Similarity	NPC193934
0.8241	Intermediate Similarity	NPC119601
0.8241	Intermediate Similarity	NPC204450
0.8241	Intermediate Similarity	NPC271980
0.8241	Intermediate Similarity	NPC56498
0.8241	Intermediate Similarity	NPC195290
0.8241	Intermediate Similarity	NPC87351
0.8241	Intermediate Similarity	NPC308726
0.823	Intermediate Similarity	NPC147180
0.8224	Intermediate Similarity	NPC474720
0.8224	Intermediate Similarity	NPC472972
0.8224	Intermediate Similarity	NPC327431
0.8224	Intermediate Similarity	NPC88198
0.8224	Intermediate Similarity	NPC83709
0.8224	Intermediate Similarity	NPC154072
0.8224	Intermediate Similarity	NPC112167
0.8214	Intermediate Similarity	NPC239097
0.8214	Intermediate Similarity	NPC129689
0.8214	Intermediate Similarity	NPC163314
0.8214	Intermediate Similarity	NPC272898
0.8214	Intermediate Similarity	NPC76084
0.8214	Intermediate Similarity	NPC235077
0.8214	Intermediate Similarity	NPC473036
0.8211	Intermediate Similarity	NPC469674
0.8208	Intermediate Similarity	NPC43747
0.8208	Intermediate Similarity	NPC226986
0.8208	Intermediate Similarity	NPC292133
0.8208	Intermediate Similarity	NPC23680
0.8198	Intermediate Similarity	NPC189075
0.8198	Intermediate Similarity	NPC217201
0.8198	Intermediate Similarity	NPC275539
0.8198	Intermediate Similarity	NPC295244
0.819	Intermediate Similarity	NPC329736
0.819	Intermediate Similarity	NPC279974
0.8182	Intermediate Similarity	NPC48733
0.8182	Intermediate Similarity	NPC319077
0.8182	Intermediate Similarity	NPC214264
0.8182	Intermediate Similarity	NPC102352
0.8182	Intermediate Similarity	NPC49958
0.8182	Intermediate Similarity	NPC97202
0.8182	Intermediate Similarity	NPC302607

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 NPC71348 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	1570
0.2-0.3	3881
0.3-0.4	2300
0.4-0.5	693
0.5-0.6	204
0.6-0.7	148
0.7-0.8	94
0.8-0.85	37
0.85-0.9	31
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9057	High Similarity	NPD6881	Approved
0.9057	High Similarity	NPD6899	Approved
0.8981	High Similarity	NPD6649	Approved
0.8981	High Similarity	NPD6650	Approved
0.8981	High Similarity	NPD8130	Phase 1
0.8962	High Similarity	NPD5697	Approved
0.8899	High Similarity	NPD8297	Approved
0.8889	High Similarity	NPD7290	Approved
0.8889	High Similarity	NPD6883	Approved
0.8889	High Similarity	NPD7102	Approved
0.8879	High Similarity	NPD6011	Approved
0.8868	High Similarity	NPD7128	Approved
0.8868	High Similarity	NPD6675	Approved
0.8868	High Similarity	NPD5739	Approved
0.8868	High Similarity	NPD6402	Approved
0.8807	High Similarity	NPD6617	Approved
0.8807	High Similarity	NPD6847	Approved
0.8807	High Similarity	NPD6869	Approved
0.8796	High Similarity	NPD6373	Approved
0.8796	High Similarity	NPD6014	Approved
0.8796	High Similarity	NPD6013	Approved
0.8796	High Similarity	NPD6012	Approved
0.8796	High Similarity	NPD6372	Approved
0.8727	High Similarity	NPD6882	Approved
0.8704	High Similarity	NPD7320	Approved
0.8649	High Similarity	NPD4632	Approved
0.8621	High Similarity	NPD7604	Phase 2
0.8611	High Similarity	NPD5701	Approved
0.8571	High Similarity	NPD4696	Approved
0.8571	High Similarity	NPD5286	Approved
0.8571	High Similarity	NPD5285	Approved
0.8519	High Similarity	NPD6008	Approved
0.8491	Intermediate Similarity	NPD5223	Approved
0.8468	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD6009	Approved
0.8411	Intermediate Similarity	NPD5225	Approved
0.8411	Intermediate Similarity	NPD5211	Phase 2
0.8411	Intermediate Similarity	NPD4633	Approved
0.8411	Intermediate Similarity	NPD5226	Approved
0.8411	Intermediate Similarity	NPD5224	Approved
0.8381	Intermediate Similarity	NPD4755	Approved
0.8362	Intermediate Similarity	NPD6319	Approved
0.8348	Intermediate Similarity	NPD6335	Approved
0.8333	Intermediate Similarity	NPD5174	Approved
0.8333	Intermediate Similarity	NPD5175	Approved
0.8291	Intermediate Similarity	NPD5983	Phase 2
0.8286	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD5222	Approved
0.8286	Intermediate Similarity	NPD5221	Approved
0.8276	Intermediate Similarity	NPD7100	Approved
0.8276	Intermediate Similarity	NPD7101	Approved
0.8261	Intermediate Similarity	NPD6317	Approved
0.8257	Intermediate Similarity	NPD5141	Approved
0.8252	Intermediate Similarity	NPD6079	Approved
0.8235	Intermediate Similarity	NPD7492	Approved
0.8224	Intermediate Similarity	NPD4700	Approved
0.8214	Intermediate Similarity	NPD4634	Approved
0.8208	Intermediate Similarity	NPD6084	Phase 2
0.8208	Intermediate Similarity	NPD5173	Approved
0.8208	Intermediate Similarity	NPD6083	Phase 2
0.8205	Intermediate Similarity	NPD6054	Approved
0.819	Intermediate Similarity	NPD6313	Approved
0.819	Intermediate Similarity	NPD6314	Approved
0.8182	Intermediate Similarity	NPD7736	Approved
0.8174	Intermediate Similarity	NPD6274	Approved
0.8173	Intermediate Similarity	NPD6399	Phase 3
0.8167	Intermediate Similarity	NPD6336	Discontinued
0.8167	Intermediate Similarity	NPD6616	Approved
0.8136	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD4697	Phase 3
0.8099	Intermediate Similarity	NPD7078	Approved
0.8067	Intermediate Similarity	NPD6370	Approved
0.8058	Intermediate Similarity	NPD5328	Approved
0.8036	Intermediate Similarity	NPD4730	Approved
0.8036	Intermediate Similarity	NPD4729	Approved
0.8019	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.8017	Intermediate Similarity	NPD6868	Approved
0.8	Intermediate Similarity	NPD4754	Approved
0.7983	Intermediate Similarity	NPD6016	Approved
0.7983	Intermediate Similarity	NPD6015	Approved
0.7963	Intermediate Similarity	NPD5696	Approved
0.7951	Intermediate Similarity	NPD8293	Discontinued
0.7917	Intermediate Similarity	NPD5988	Approved
0.7899	Intermediate Similarity	NPD6059	Approved
0.7895	Intermediate Similarity	NPD5169	Approved
0.7895	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD5247	Approved
0.7895	Intermediate Similarity	NPD5135	Approved
0.7895	Intermediate Similarity	NPD5250	Approved
0.7895	Intermediate Similarity	NPD5248	Approved
0.7895	Intermediate Similarity	NPD5251	Approved
0.7895	Intermediate Similarity	NPD5249	Phase 3
0.7876	Intermediate Similarity	NPD5128	Approved
0.787	Intermediate Similarity	NPD7902	Approved
0.7857	Intermediate Similarity	NPD4768	Approved
0.7857	Intermediate Similarity	NPD4767	Approved
0.785	Intermediate Similarity	NPD5210	Approved
0.785	Intermediate Similarity	NPD5695	Phase 3
0.785	Intermediate Similarity	NPD4629	Approved
0.7833	Intermediate Similarity	NPD6909	Approved
0.7833	Intermediate Similarity	NPD6908	Approved
0.783	Intermediate Similarity	NPD4202	Approved
0.7826	Intermediate Similarity	NPD5216	Approved
0.7826	Intermediate Similarity	NPD5127	Approved
0.7826	Intermediate Similarity	NPD5215	Approved
0.7826	Intermediate Similarity	NPD5217	Approved
0.7798	Intermediate Similarity	NPD7638	Approved
0.7797	Intermediate Similarity	NPD7115	Discovery
0.7788	Intermediate Similarity	NPD5737	Approved
0.7788	Intermediate Similarity	NPD6672	Approved
0.7767	Intermediate Similarity	NPD7521	Approved
0.7767	Intermediate Similarity	NPD7334	Approved
0.7767	Intermediate Similarity	NPD3618	Phase 1
0.7767	Intermediate Similarity	NPD6684	Approved
0.7767	Intermediate Similarity	NPD5330	Approved
0.7767	Intermediate Similarity	NPD6409	Approved
0.7767	Intermediate Similarity	NPD7146	Approved
0.7757	Intermediate Similarity	NPD7748	Approved
0.7727	Intermediate Similarity	NPD7640	Approved
0.7727	Intermediate Similarity	NPD7639	Approved
0.7714	Intermediate Similarity	NPD6904	Approved
0.7714	Intermediate Similarity	NPD6673	Approved
0.7714	Intermediate Similarity	NPD6080	Approved
0.7714	Intermediate Similarity	NPD4753	Phase 2
0.7627	Intermediate Similarity	NPD5167	Approved
0.7619	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6903	Approved
0.7593	Intermediate Similarity	NPD6001	Approved
0.7593	Intermediate Similarity	NPD7900	Approved
0.7593	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD3666	Approved
0.7573	Intermediate Similarity	NPD3133	Approved
0.7573	Intermediate Similarity	NPD4786	Approved
0.7573	Intermediate Similarity	NPD3665	Phase 1
0.757	Intermediate Similarity	NPD5281	Approved
0.757	Intermediate Similarity	NPD8034	Phase 2
0.757	Intermediate Similarity	NPD7515	Phase 2
0.757	Intermediate Similarity	NPD5284	Approved
0.757	Intermediate Similarity	NPD8035	Phase 2
0.7565	Intermediate Similarity	NPD5168	Approved
0.75	Intermediate Similarity	NPD5329	Approved
0.7478	Intermediate Similarity	NPD6412	Phase 2
0.746	Intermediate Similarity	NPD6033	Approved
0.7429	Intermediate Similarity	NPD6098	Approved
0.7429	Intermediate Similarity	NPD5690	Phase 2
0.7419	Intermediate Similarity	NPD8328	Phase 3
0.7407	Intermediate Similarity	NPD6050	Approved
0.7407	Intermediate Similarity	NPD5693	Phase 1
0.7407	Intermediate Similarity	NPD5694	Approved
0.7404	Intermediate Similarity	NPD4197	Approved
0.7379	Intermediate Similarity	NPD3667	Approved
0.7358	Intermediate Similarity	NPD3573	Approved
0.7348	Intermediate Similarity	NPD6334	Approved
0.7348	Intermediate Similarity	NPD6333	Approved
0.7315	Intermediate Similarity	NPD5692	Phase 3
0.7311	Intermediate Similarity	NPD6053	Discontinued
0.7302	Intermediate Similarity	NPD7507	Approved
0.7264	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5279	Phase 3
0.7212	Intermediate Similarity	NPD4223	Phase 3
0.7212	Intermediate Similarity	NPD4221	Approved
0.7179	Intermediate Similarity	NPD6614	Approved
0.717	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5207	Approved
0.7132	Intermediate Similarity	NPD7319	Approved
0.713	Intermediate Similarity	NPD7632	Discontinued
0.713	Intermediate Similarity	NPD5208	Approved
0.7119	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4694	Approved
0.7103	Intermediate Similarity	NPD5280	Approved
0.7091	Intermediate Similarity	NPD6411	Approved
0.708	Intermediate Similarity	NPD5959	Approved
0.7073	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6435	Approved
0.7023	Intermediate Similarity	NPD7260	Phase 2
0.7019	Intermediate Similarity	NPD4695	Discontinued
0.7008	Intermediate Similarity	NPD6067	Discontinued
0.7	Intermediate Similarity	NPD5785	Approved
0.6983	Remote Similarity	NPD5091	Approved
0.6981	Remote Similarity	NPD4788	Approved
0.696	Remote Similarity	NPD4522	Approved
0.6944	Remote Similarity	NPD4693	Phase 3
0.6944	Remote Similarity	NPD4689	Approved
0.6944	Remote Similarity	NPD4690	Approved
0.6944	Remote Similarity	NPD5205	Approved
0.6944	Remote Similarity	NPD4688	Approved
0.6944	Remote Similarity	NPD4138	Approved
0.6923	Remote Similarity	NPD4195	Approved
0.6917	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD3668	Phase 3
0.6909	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6101	Approved
0.6903	Remote Similarity	NPD5654	Approved
0.6875	Remote Similarity	NPD5779	Approved
0.6875	Remote Similarity	NPD5133	Approved
0.6875	Remote Similarity	NPD5778	Approved
0.687	Remote Similarity	NPD4225	Approved
0.686	Remote Similarity	NPD5955	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