NPASS Compound

Structure

NPC271266 OpenBabel07101719142D 39 43 0 0 1 0 0 0 0 0999 V2000 -4.8973 -5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2500 -5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9703 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2709 1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9847 -4.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 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 2.5981 0.5000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6102 -4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 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 -3.9192 -5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9921 -2.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7709 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6757 -3.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6320 -3.9543 0.0000 C 0 0 0 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 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3230 -3.0032 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -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 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7709 0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3024 -3.3305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9629 -4.6974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2709 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3448 -2.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 5 21 1 0 0 0 0 6 22 1 0 0 0 0 7 30 1 0 0 0 0 9 10 1 0 0 0 0 9 23 1 0 0 0 0 10 27 1 0 0 0 0 11 12 2 0 0 0 0 11 24 1 0 0 0 0 12 32 1 0 0 0 0 13 14 1 0 0 0 0 13 30 1 0 0 0 0 15 18 2 0 0 0 0 15 25 1 0 0 0 0 16 26 1 0 0 0 0 16 31 1 0 0 0 0 17 32 1 0 0 0 0 17 33 1 0 0 0 0 19 3 1 6 0 0 0 19 23 1 0 0 0 0 19 24 1 0 0 0 0 20 4 1 1 0 0 0 20 28 1 0 0 0 0 20 29 1 0 0 0 0 21 34 2 0 0 0 0 21 38 1 0 0 0 0 22 35 2 0 0 0 0 22 39 1 0 0 0 0 23 32 1 1 0 0 0 24 36 2 0 0 0 0 25 37 2 0 0 0 0 26 28 1 0 0 0 0 26 38 1 1 0 0 0 27 31 1 6 0 0 0 27 33 1 0 0 0 0 28 30 1 1 0 0 0 29 25 1 1 0 0 0 29 39 1 0 0 0 0 30 31 1 1 0 0 0 31 8 1 6 0 0 0 32 33 1 6 0 0 0 33 14 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	538.33
Volume:	573.464
LogP:	4.489
LogD:	3.643
LogS:	-5.008
# Rotatable Bonds:	8
TPSA:	86.74
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.303
Synthetic Accessibility Score:	6.095
Fsp3:	0.758
Lipinski Rule-of-5:	Accepted
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:	-5.152
MDCK Permeability:	2.274125290568918e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.208
Plasma Protein Binding (PPB):	84.36556243896484%
Volume Distribution (VD):	1.708
Pgp-substrate:	8.399535179138184%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.3
CYP2C19-inhibitor:	0.101
CYP2C19-substrate:	0.835
CYP2C9-inhibitor:	0.167
CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.075
CYP2D6-substrate:	0.038
CYP3A4-inhibitor:	0.903
CYP3A4-substrate:	0.803

ADMET: Excretion

Clearance (CL):	3.033
Half-life (T1/2):	0.344

ADMET: Toxicity

hERG Blockers:	0.448
Human Hepatotoxicity (H-HT):	0.502
Drug-inuced Liver Injury (DILI):	0.766
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.933
Maximum Recommended Daily Dose:	0.918
Skin Sensitization:	0.948
Carcinogencity:	0.746
Eye Corrosion:	0.01
Eye Irritation:	0.023
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC271266

Natural Product ID:	NPC271266
*Common Name:**	GJYVHBNHRSKXSV-TTXOOTMKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GJYVHBNHRSKXSV-TTXOOTMKSA-N
Standard InCHI:	InChI=1S/C33H46O6/c1-18(2)15-25(37)29(39-22(6)35)20(4)28-26(38-21(5)34)16-31(8)27-10-9-23-19(3)24(36)11-12-32(23)17-33(27,32)14-13-30(28,31)7/h11-12,15,19-20,23,26-29H,9-10,13-14,16-17H2,1-8H3/t19-,20-,23-,26-,27-,28-,29+,30+,31-,32+,33-/m0/s1
SMILES:	CC(=CC(=O)[C@@H]([C@@H](C)[C@H]1[C@H](C[C@@]2(C)[C@@H]3CC[C@H]4[C@H](C)C(=O)C=C[C@]54C[C@@]35CC[C@]12C)OC(=O)C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1941163
PubChem CID:	57332505
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	6

Activity Type	# Activity
Others	8

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	FC	=	44.0	n.a.	PMID[508078]
NPT2	Others	Unspecified	FC	=	34.0	n.a.	PMID[508078]
NPT2	Others	Unspecified	FC	=	1.1	n.a.	PMID[508078]
NPT2	Others	Unspecified	IC50	>	1000000.0	nM	PMID[508078]
NPT2	Others	Unspecified	FC	=	44.0	n.a.	PMID[508079]
NPT2	Others	Unspecified	FC	=	34.0	n.a.	PMID[508079]
NPT2	Others	Unspecified	FC	=	1.1	n.a.	PMID[508079]

☑ 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 NPC271266 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	246
0.1-0.2	1421
0.2-0.3	6145
0.3-0.4	13647
0.4-0.5	7663
0.5-0.6	7090
0.6-0.7	5189
0.7-0.8	1222
0.8-0.85	56
0.85-0.9	6
0.9-0.95	7
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC308351
0.9691	High Similarity	NPC470267
0.9495	High Similarity	NPC470269
0.949	High Similarity	NPC181265
0.9388	High Similarity	NPC235889
0.9216	High Similarity	NPC118860
0.9216	High Similarity	NPC214797
0.9216	High Similarity	NPC231589
0.9208	High Similarity	NPC258543
0.9208	High Similarity	NPC241927
0.9126	High Similarity	NPC170487
0.8942	High Similarity	NPC71348
0.8868	High Similarity	NPC270958
0.8704	High Similarity	NPC118638
0.8679	High Similarity	NPC202889
0.866	High Similarity	NPC294266
0.8646	High Similarity	NPC218301
0.8641	High Similarity	NPC44063
0.8632	High Similarity	NPC305039
0.8544	High Similarity	NPC475571
0.8511	High Similarity	NPC195640
0.85	High Similarity	NPC176845
0.8485	Intermediate Similarity	NPC111684
0.8485	Intermediate Similarity	NPC58052
0.8476	Intermediate Similarity	NPC2766
0.8462	Intermediate Similarity	NPC475294
0.8447	Intermediate Similarity	NPC310586
0.8431	Intermediate Similarity	NPC15396
0.8411	Intermediate Similarity	NPC475524
0.8411	Intermediate Similarity	NPC100267
0.8404	Intermediate Similarity	NPC323765
0.8396	Intermediate Similarity	NPC197428
0.8384	Intermediate Similarity	NPC33473
0.8367	Intermediate Similarity	NPC477361
0.8367	Intermediate Similarity	NPC202824
0.8367	Intermediate Similarity	NPC79117
0.8333	Intermediate Similarity	NPC310981
0.8318	Intermediate Similarity	NPC43775
0.8316	Intermediate Similarity	NPC264127
0.83	Intermediate Similarity	NPC477354
0.8269	Intermediate Similarity	NPC228669
0.8269	Intermediate Similarity	NPC164835
0.8241	Intermediate Similarity	NPC221144
0.8218	Intermediate Similarity	NPC226986
0.8218	Intermediate Similarity	NPC292133
0.8218	Intermediate Similarity	NPC23680
0.8208	Intermediate Similarity	NPC94529
0.82	Intermediate Similarity	NPC470974
0.82	Intermediate Similarity	NPC470978
0.82	Intermediate Similarity	NPC469599
0.819	Intermediate Similarity	NPC265127
0.819	Intermediate Similarity	NPC470309
0.8182	Intermediate Similarity	NPC148458
0.8182	Intermediate Similarity	NPC109414
0.8155	Intermediate Similarity	NPC99411
0.8144	Intermediate Similarity	NPC472220
0.8144	Intermediate Similarity	NPC28227
0.8144	Intermediate Similarity	NPC97884
0.8137	Intermediate Similarity	NPC197386
0.8137	Intermediate Similarity	NPC275439
0.8137	Intermediate Similarity	NPC98868
0.8137	Intermediate Similarity	NPC471582
0.8137	Intermediate Similarity	NPC112753
0.8131	Intermediate Similarity	NPC304495
0.8119	Intermediate Similarity	NPC42042
0.8108	Intermediate Similarity	NPC239273
0.8108	Intermediate Similarity	NPC471854
0.8095	Intermediate Similarity	NPC137657
0.8085	Intermediate Similarity	NPC100297
0.8081	Intermediate Similarity	NPC154101
0.8077	Intermediate Similarity	NPC87351
0.8077	Intermediate Similarity	NPC473928
0.8073	Intermediate Similarity	NPC264634
0.8061	Intermediate Similarity	NPC177141
0.8058	Intermediate Similarity	NPC144956
0.8039	Intermediate Similarity	NPC87090
0.8039	Intermediate Similarity	NPC216904
0.8037	Intermediate Similarity	NPC211224
0.8036	Intermediate Similarity	NPC257457
0.8036	Intermediate Similarity	NPC311554
0.8019	Intermediate Similarity	NPC196528
0.8019	Intermediate Similarity	NPC231530
0.8019	Intermediate Similarity	NPC278628
0.8	Intermediate Similarity	NPC236390
0.8	Intermediate Similarity	NPC311612
0.8	Intermediate Similarity	NPC36321
0.7982	Intermediate Similarity	NPC470281
0.7981	Intermediate Similarity	NPC476240
0.7981	Intermediate Similarity	NPC224720
0.7981	Intermediate Similarity	NPC477356
0.7981	Intermediate Similarity	NPC474327
0.7981	Intermediate Similarity	NPC476223
0.798	Intermediate Similarity	NPC474842
0.798	Intermediate Similarity	NPC475965
0.7961	Intermediate Similarity	NPC222011
0.7961	Intermediate Similarity	NPC271387
0.7961	Intermediate Similarity	NPC252295
0.7961	Intermediate Similarity	NPC153792
0.7961	Intermediate Similarity	NPC114274
0.7961	Intermediate Similarity	NPC477355
0.7944	Intermediate Similarity	NPC220974
0.7941	Intermediate Similarity	NPC322063
0.7941	Intermediate Similarity	NPC328162
0.7941	Intermediate Similarity	NPC305483
0.7941	Intermediate Similarity	NPC471775
0.7941	Intermediate Similarity	NPC96859
0.7925	Intermediate Similarity	NPC29705
0.7925	Intermediate Similarity	NPC255309
0.7925	Intermediate Similarity	NPC189616
0.7925	Intermediate Similarity	NPC13385
0.7909	Intermediate Similarity	NPC147180
0.7905	Intermediate Similarity	NPC195290
0.7905	Intermediate Similarity	NPC56498
0.7905	Intermediate Similarity	NPC204450
0.7905	Intermediate Similarity	NPC118405
0.7905	Intermediate Similarity	NPC53222
0.7905	Intermediate Similarity	NPC308726
0.7905	Intermediate Similarity	NPC119601
0.7905	Intermediate Similarity	NPC136289
0.7905	Intermediate Similarity	NPC22388
0.79	Intermediate Similarity	NPC470113
0.7895	Intermediate Similarity	NPC321289
0.7895	Intermediate Similarity	NPC327969
0.7885	Intermediate Similarity	NPC476274
0.7885	Intermediate Similarity	NPC218383
0.7879	Intermediate Similarity	NPC477943
0.7879	Intermediate Similarity	NPC474570
0.7879	Intermediate Similarity	NPC474679
0.7864	Intermediate Similarity	NPC57416
0.7864	Intermediate Similarity	NPC43747
0.7864	Intermediate Similarity	NPC84335
0.7864	Intermediate Similarity	NPC18319
0.7864	Intermediate Similarity	NPC151488
0.7864	Intermediate Similarity	NPC108078
0.7864	Intermediate Similarity	NPC69385
0.7864	Intermediate Similarity	NPC18509
0.7864	Intermediate Similarity	NPC107243
0.7864	Intermediate Similarity	NPC38530
0.785	Intermediate Similarity	NPC96377
0.785	Intermediate Similarity	NPC127790
0.7843	Intermediate Similarity	NPC317586
0.7843	Intermediate Similarity	NPC293052
0.7843	Intermediate Similarity	NPC470016
0.7843	Intermediate Similarity	NPC476174
0.7838	Intermediate Similarity	NPC472929
0.7838	Intermediate Similarity	NPC472926
0.7835	Intermediate Similarity	NPC29447
0.7835	Intermediate Similarity	NPC470223
0.783	Intermediate Similarity	NPC111323
0.783	Intermediate Similarity	NPC474330
0.783	Intermediate Similarity	NPC474207
0.783	Intermediate Similarity	NPC470310
0.783	Intermediate Similarity	NPC140723
0.783	Intermediate Similarity	NPC470954
0.7822	Intermediate Similarity	NPC25750
0.7822	Intermediate Similarity	NPC206810
0.7818	Intermediate Similarity	NPC470960
0.781	Intermediate Similarity	NPC163372
0.781	Intermediate Similarity	NPC124211
0.781	Intermediate Similarity	NPC81530
0.781	Intermediate Similarity	NPC302537
0.78	Intermediate Similarity	NPC273199
0.78	Intermediate Similarity	NPC471896
0.7798	Intermediate Similarity	NPC41405
0.7788	Intermediate Similarity	NPC235464
0.7788	Intermediate Similarity	NPC477854
0.7788	Intermediate Similarity	NPC147954
0.7788	Intermediate Similarity	NPC166745
0.7778	Intermediate Similarity	NPC470612
0.7778	Intermediate Similarity	NPC185
0.7778	Intermediate Similarity	NPC470613
0.7778	Intermediate Similarity	NPC471601
0.7768	Intermediate Similarity	NPC471398
0.7767	Intermediate Similarity	NPC328371
0.7767	Intermediate Similarity	NPC125622
0.7767	Intermediate Similarity	NPC307164
0.7757	Intermediate Similarity	NPC135854
0.7757	Intermediate Similarity	NPC470251
0.7757	Intermediate Similarity	NPC119493
0.7757	Intermediate Similarity	NPC216245
0.7757	Intermediate Similarity	NPC2436
0.7755	Intermediate Similarity	NPC327115
0.7755	Intermediate Similarity	NPC220478
0.7755	Intermediate Similarity	NPC471042
0.7748	Intermediate Similarity	NPC280782
0.7745	Intermediate Similarity	NPC471078
0.7745	Intermediate Similarity	NPC473435
0.7745	Intermediate Similarity	NPC166906
0.7745	Intermediate Similarity	NPC473280
0.7745	Intermediate Similarity	NPC124207
0.7745	Intermediate Similarity	NPC473431
0.7745	Intermediate Similarity	NPC56525
0.7736	Intermediate Similarity	NPC473163
0.7736	Intermediate Similarity	NPC475320
0.7732	Intermediate Similarity	NPC109512
0.7732	Intermediate Similarity	NPC320801
0.7732	Intermediate Similarity	NPC100391
0.7727	Intermediate Similarity	NPC473627
0.7723	Intermediate Similarity	NPC168027
0.7723	Intermediate Similarity	NPC185936

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 NPC271266 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	1643
0.2-0.3	4108
0.3-0.4	2166
0.4-0.5	578
0.5-0.6	189
0.6-0.7	96
0.7-0.8	109
0.8-0.85	45
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8738	High Similarity	NPD6899	Approved
0.8738	High Similarity	NPD6881	Approved
0.8723	High Similarity	NPD5737	Approved
0.8723	High Similarity	NPD6672	Approved
0.8667	High Similarity	NPD8130	Phase 1
0.8641	High Similarity	NPD5697	Approved
0.8632	High Similarity	NPD6673	Approved
0.8632	High Similarity	NPD6080	Approved
0.8632	High Similarity	NPD6904	Approved
0.8585	High Similarity	NPD8297	Approved
0.8571	High Similarity	NPD7290	Approved
0.8571	High Similarity	NPD6883	Approved
0.8571	High Similarity	NPD7102	Approved
0.8558	High Similarity	NPD6011	Approved
0.8544	High Similarity	NPD6675	Approved
0.8544	High Similarity	NPD6402	Approved
0.8544	High Similarity	NPD5739	Approved
0.8544	High Similarity	NPD7128	Approved
0.8511	High Similarity	NPD7334	Approved
0.8511	High Similarity	NPD7146	Approved
0.8511	High Similarity	NPD6684	Approved
0.8511	High Similarity	NPD6409	Approved
0.8511	High Similarity	NPD7521	Approved
0.8511	High Similarity	NPD5330	Approved
0.8491	Intermediate Similarity	NPD6847	Approved
0.8491	Intermediate Similarity	NPD6869	Approved
0.8491	Intermediate Similarity	NPD6649	Approved
0.8491	Intermediate Similarity	NPD6617	Approved
0.8491	Intermediate Similarity	NPD6650	Approved
0.8476	Intermediate Similarity	NPD6014	Approved
0.8476	Intermediate Similarity	NPD6013	Approved
0.8476	Intermediate Similarity	NPD6012	Approved
0.8411	Intermediate Similarity	NPD6882	Approved
0.84	Intermediate Similarity	NPD6084	Phase 2
0.84	Intermediate Similarity	NPD6083	Phase 2
0.8381	Intermediate Similarity	NPD7320	Approved
0.8333	Intermediate Similarity	NPD6903	Approved
0.8333	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8316	Intermediate Similarity	NPD6098	Approved
0.8302	Intermediate Similarity	NPD6372	Approved
0.8302	Intermediate Similarity	NPD6373	Approved
0.8286	Intermediate Similarity	NPD5701	Approved
0.8265	Intermediate Similarity	NPD5693	Phase 1
0.8265	Intermediate Similarity	NPD6050	Approved
0.8265	Intermediate Similarity	NPD5694	Approved
0.82	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD5695	Phase 3
0.819	Intermediate Similarity	NPD6008	Approved
0.8163	Intermediate Similarity	NPD5692	Phase 3
0.8148	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD5696	Approved
0.8058	Intermediate Similarity	NPD5286	Approved
0.8058	Intermediate Similarity	NPD5285	Approved
0.8058	Intermediate Similarity	NPD4696	Approved
0.8036	Intermediate Similarity	NPD6335	Approved
0.8	Intermediate Similarity	NPD7604	Phase 2
0.8	Intermediate Similarity	NPD6399	Phase 3
0.7981	Intermediate Similarity	NPD5223	Approved
0.7965	Intermediate Similarity	NPD7100	Approved
0.7965	Intermediate Similarity	NPD7101	Approved
0.7946	Intermediate Similarity	NPD6317	Approved
0.7905	Intermediate Similarity	NPD5225	Approved
0.7905	Intermediate Similarity	NPD5226	Approved
0.7905	Intermediate Similarity	NPD4633	Approved
0.7905	Intermediate Similarity	NPD5224	Approved
0.7905	Intermediate Similarity	NPD5211	Phase 2
0.7876	Intermediate Similarity	NPD6313	Approved
0.7876	Intermediate Similarity	NPD6314	Approved
0.7864	Intermediate Similarity	NPD5959	Approved
0.7864	Intermediate Similarity	NPD4755	Approved
0.7857	Intermediate Similarity	NPD6274	Approved
0.7838	Intermediate Similarity	NPD4632	Approved
0.783	Intermediate Similarity	NPD5175	Approved
0.783	Intermediate Similarity	NPD5174	Approved
0.7788	Intermediate Similarity	NPD6009	Approved
0.7778	Intermediate Similarity	NPD6614	Approved
0.7778	Intermediate Similarity	NPD5208	Approved
0.7767	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD5222	Approved
0.7767	Intermediate Similarity	NPD5221	Approved
0.7757	Intermediate Similarity	NPD5141	Approved
0.7745	Intermediate Similarity	NPD6001	Approved
0.7739	Intermediate Similarity	NPD6319	Approved
0.7723	Intermediate Similarity	NPD6079	Approved
0.7714	Intermediate Similarity	NPD4700	Approved
0.77	Intermediate Similarity	NPD4753	Phase 2
0.7699	Intermediate Similarity	NPD6868	Approved
0.7692	Intermediate Similarity	NPD5173	Approved
0.7672	Intermediate Similarity	NPD5983	Phase 2
0.767	Intermediate Similarity	NPD5654	Approved
0.767	Intermediate Similarity	NPD5210	Approved
0.767	Intermediate Similarity	NPD4629	Approved
0.7653	Intermediate Similarity	NPD5329	Approved
0.7627	Intermediate Similarity	NPD7492	Approved
0.7624	Intermediate Similarity	NPD5207	Approved
0.7586	Intermediate Similarity	NPD6054	Approved
0.7583	Intermediate Similarity	NPD7736	Approved
0.7576	Intermediate Similarity	NPD5690	Phase 2
0.7573	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD7900	Approved
0.7563	Intermediate Similarity	NPD6336	Discontinued
0.7563	Intermediate Similarity	NPD6616	Approved
0.7551	Intermediate Similarity	NPD3665	Phase 1
0.7551	Intermediate Similarity	NPD3666	Approved
0.7551	Intermediate Similarity	NPD3133	Approved
0.7551	Intermediate Similarity	NPD4197	Approved
0.7549	Intermediate Similarity	NPD5284	Approved
0.7549	Intermediate Similarity	NPD5281	Approved
0.7545	Intermediate Similarity	NPD4729	Approved
0.7545	Intermediate Similarity	NPD4730	Approved
0.7525	Intermediate Similarity	NPD5328	Approved
0.7521	Intermediate Similarity	NPD6909	Approved
0.7521	Intermediate Similarity	NPD6908	Approved
0.7521	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3573	Approved
0.75	Intermediate Similarity	NPD7078	Approved
0.75	Intermediate Similarity	NPD4754	Approved
0.7458	Intermediate Similarity	NPD6370	Approved
0.7429	Intermediate Similarity	NPD4697	Phase 3
0.7411	Intermediate Similarity	NPD4634	Approved
0.7411	Intermediate Similarity	NPD5251	Approved
0.7411	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD5249	Phase 3
0.7411	Intermediate Similarity	NPD5247	Approved
0.7411	Intermediate Similarity	NPD5169	Approved
0.7411	Intermediate Similarity	NPD5135	Approved
0.7411	Intermediate Similarity	NPD5248	Approved
0.7411	Intermediate Similarity	NPD5250	Approved
0.7404	Intermediate Similarity	NPD7748	Approved
0.7387	Intermediate Similarity	NPD5128	Approved
0.7374	Intermediate Similarity	NPD4786	Approved
0.7373	Intermediate Similarity	NPD6015	Approved
0.7373	Intermediate Similarity	NPD6016	Approved
0.7364	Intermediate Similarity	NPD4767	Approved
0.7364	Intermediate Similarity	NPD4768	Approved
0.7358	Intermediate Similarity	NPD7902	Approved
0.7355	Intermediate Similarity	NPD8293	Discontinued
0.7347	Intermediate Similarity	NPD4223	Phase 3
0.7347	Intermediate Similarity	NPD4221	Approved
0.7345	Intermediate Similarity	NPD5217	Approved
0.7345	Intermediate Similarity	NPD5215	Approved
0.7345	Intermediate Similarity	NPD5127	Approved
0.7345	Intermediate Similarity	NPD5216	Approved
0.7311	Intermediate Similarity	NPD5988	Approved
0.7308	Intermediate Similarity	NPD4202	Approved
0.7288	Intermediate Similarity	NPD6059	Approved
0.7228	Intermediate Similarity	NPD5279	Phase 3
0.7228	Intermediate Similarity	NPD4694	Approved
0.7228	Intermediate Similarity	NPD5280	Approved
0.72	Intermediate Similarity	NPD3668	Phase 3
0.7184	Intermediate Similarity	NPD6051	Approved
0.7182	Intermediate Similarity	NPD6052	Approved
0.7179	Intermediate Similarity	NPD7115	Discovery
0.7172	Intermediate Similarity	NPD3667	Approved
0.7172	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD5167	Approved
0.7143	Intermediate Similarity	NPD6412	Phase 2
0.7143	Intermediate Similarity	NPD4695	Discontinued
0.708	Intermediate Similarity	NPD5168	Approved
0.7059	Intermediate Similarity	NPD4689	Approved
0.7059	Intermediate Similarity	NPD4690	Approved
0.7059	Intermediate Similarity	NPD5205	Approved
0.7059	Intermediate Similarity	NPD4138	Approved
0.7059	Intermediate Similarity	NPD4688	Approved
0.7059	Intermediate Similarity	NPD3618	Phase 1
0.7059	Intermediate Similarity	NPD4693	Phase 3
0.7048	Intermediate Similarity	NPD8034	Phase 2
0.7048	Intermediate Similarity	NPD8035	Phase 2
0.7048	Intermediate Similarity	NPD7515	Phase 2
0.7041	Intermediate Similarity	NPD4195	Approved
0.7019	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6435	Approved
0.6983	Remote Similarity	NPD6053	Discontinued
0.6981	Remote Similarity	NPD5133	Approved
0.6972	Remote Similarity	NPD7638	Approved
0.6961	Remote Similarity	NPD1694	Approved
0.6944	Remote Similarity	NPD7732	Phase 3
0.6939	Remote Similarity	NPD3617	Approved
0.6937	Remote Similarity	NPD5091	Approved
0.6931	Remote Similarity	NPD4788	Approved
0.6923	Remote Similarity	NPD7094	Approved
0.6923	Remote Similarity	NPD6858	Approved
0.6915	Remote Similarity	NPD4691	Approved
0.6915	Remote Similarity	NPD4747	Approved
0.6909	Remote Similarity	NPD7639	Approved
0.6909	Remote Similarity	NPD7640	Approved
0.6893	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6411	Approved
0.688	Remote Similarity	NPD6033	Approved
0.6875	Remote Similarity	NPD4058	Approved
0.6842	Remote Similarity	NPD5777	Approved
0.6809	Remote Similarity	NPD4137	Phase 3
0.68	Remote Similarity	NPD5368	Approved
0.6794	Remote Similarity	NPD6333	Approved
0.6794	Remote Similarity	NPD6334	Approved
0.6792	Remote Similarity	NPD5785	Approved
0.6701	Remote Similarity	NPD4687	Approved
0.6701	Remote Similarity	NPD5733	Approved
0.6698	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6101	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