NPASS Compound

Structure

NPC471901 OpenBabel07101718302D 36 40 0 0 1 0 0 0 0 0999 V2000 4.7183 0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1112 1.4666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 4.3902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1379 -2.3547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5103 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0360 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4626 -1.7649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7640 0.7415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 3.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4626 -0.1863 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6898 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6898 0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5347 2.4390 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5347 -0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0225 0.6185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -1.4634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8449 1.4634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8449 -0.4878 0.0000 C 0 0 1 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 -2.5347 1.4634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2245 4.3902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9981 0.6185 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 -0.2264 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 2.9268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 6 30 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 16 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 25 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 31 1 0 0 0 0 17 18 1 0 0 0 0 17 28 1 0 0 0 0 18 30 1 0 0 0 0 20 33 2 0 0 0 0 20 36 1 0 0 0 0 21 19 1 6 0 0 0 21 26 1 0 0 0 0 22 26 1 0 0 0 0 22 30 1 6 0 0 0 23 29 1 1 0 0 0 23 31 1 0 0 0 0 24 29 1 1 0 0 0 24 32 1 0 0 0 0 25 32 1 1 0 0 0 25 36 1 0 0 0 0 26 28 1 1 0 0 0 27 32 1 0 0 0 0 27 34 2 0 0 0 0 27 35 1 0 0 0 0 28 4 1 1 0 0 0 29 5 1 1 0 0 0 30 31 1 1 0 0 0 31 7 1 1 0 0 0 32 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.37
Volume:	546.497
LogP:	5.341
LogD:	5.047
LogS:	-4.754
# Rotatable Bonds:	4
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.32
Synthetic Accessibility Score:	4.879
Fsp3:	0.875
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.248
MDCK Permeability:	8.249463280662894e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.683

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	91.5213851928711%
Volume Distribution (VD):	0.886
Pgp-substrate:	2.343862771987915%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.466
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.947
CYP2C9-inhibitor:	0.133
CYP2C9-substrate:	0.759
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.354
CYP3A4-inhibitor:	0.218
CYP3A4-substrate:	0.284

ADMET: Excretion

Clearance (CL):	1.948
Half-life (T1/2):	0.337

ADMET: Toxicity

hERG Blockers:	0.121
Human Hepatotoxicity (H-HT):	0.163
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.149
Skin Sensitization:	0.854
Carcinogencity:	0.007
Eye Corrosion:	0.988
Eye Irritation:	0.927
Respiratory Toxicity:	0.474

Download Data

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

Natural Product: NPC471901

Natural Product ID:	NPC471901
*Common Name:**	3-O-Acetyl-Lupeolic Acid
IUPAC Name:	(1R,3aR,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bR)-9-acetyloxy-3a,5a,5b,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-8-carboxylic acid
Synonyms:
Standard InCHIKey:	DULLEXJVWYWBKQ-VDHVTXALSA-N
Standard InCHI:	InChI=1S/C32H50O4/c1-19(2)21-11-14-28(4)17-18-30(6)22(26(21)28)9-10-23-29(5)15-13-25(36-20(3)33)32(8,27(34)35)24(29)12-16-31(23,30)7/h21-26H,1,9-18H2,2-8H3,(H,34,35)/t21-,22+,23+,24+,25-,26+,28+,29+,30+,31+,32+/m0/s1
SMILES:	CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C(=O)O)OC(=O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3289106
PubChem CID:	90644331
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO33055	boswellia spp.	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24844534]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	6
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	4
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT136	Cell Line	SK-N-SH	Homo sapiens	IC50	=	4100.0	nM	PMID[465307]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	>	10000.0	nM	PMID[465307]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	>	10000.0	nM	PMID[465307]
NPT956	Individual Protein	Prostaglandin E synthase	Homo sapiens	Activity	=	51.4	%	PMID[465307]
NPT956	Individual Protein	Prostaglandin E synthase	Homo sapiens	IC50	=	10000.0	nM	PMID[465307]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4100.0	nM	PMID[465307]

☑ 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 NPC471901 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	208
0.1-0.2	1687
0.2-0.3	6137
0.3-0.4	15109
0.4-0.5	6834
0.5-0.6	5037
0.6-0.7	4734
0.7-0.8	2582
0.8-0.85	284
0.85-0.9	57
0.9-0.95	20
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9884	High Similarity	NPC287118
0.9884	High Similarity	NPC471902
0.9884	High Similarity	NPC473690
0.9767	High Similarity	NPC475416
0.9647	High Similarity	NPC4309
0.9535	High Similarity	NPC213832
0.9535	High Similarity	NPC57954
0.9419	High Similarity	NPC471900
0.9318	High Similarity	NPC160506
0.9302	High Similarity	NPC269360
0.9302	High Similarity	NPC264005
0.9302	High Similarity	NPC33768
0.9294	High Similarity	NPC98270
0.9205	High Similarity	NPC169933
0.9186	High Similarity	NPC12774
0.9186	High Similarity	NPC2783
0.9176	High Similarity	NPC475509
0.9121	High Similarity	NPC327788
0.907	High Similarity	NPC264317
0.907	High Similarity	NPC294438
0.9059	High Similarity	NPC471037
0.9011	High Similarity	NPC205173
0.8977	High Similarity	NPC474719
0.8977	High Similarity	NPC146937
0.8977	High Similarity	NPC16377
0.8925	High Similarity	NPC472028
0.8901	High Similarity	NPC78580
0.8901	High Similarity	NPC184006
0.8901	High Similarity	NPC23621
0.8876	High Similarity	NPC271974
0.8876	High Similarity	NPC220498
0.8876	High Similarity	NPC247312
0.8864	High Similarity	NPC134197
0.8851	High Similarity	NPC201655
0.8837	High Similarity	NPC5280
0.883	High Similarity	NPC94906
0.8817	High Similarity	NPC253586
0.8804	High Similarity	NPC195715
0.8804	High Similarity	NPC23241
0.8804	High Similarity	NPC210214
0.8791	High Similarity	NPC475061
0.8778	High Similarity	NPC471896
0.875	High Similarity	NPC168231
0.8737	High Similarity	NPC75941
0.871	High Similarity	NPC120708
0.8706	High Similarity	NPC261616
0.8706	High Similarity	NPC304194
0.8696	High Similarity	NPC47853
0.8696	High Similarity	NPC303863
0.8696	High Similarity	NPC277399
0.8667	High Similarity	NPC474889
0.8652	High Similarity	NPC57469
0.8646	High Similarity	NPC124544
0.8632	High Similarity	NPC108371
0.8621	High Similarity	NPC472743
0.8621	High Similarity	NPC475726
0.8617	High Similarity	NPC26413
0.8602	High Similarity	NPC279974
0.8602	High Similarity	NPC263135
0.8602	High Similarity	NPC470229
0.8602	High Similarity	NPC288906
0.8602	High Similarity	NPC266431
0.8588	High Similarity	NPC305835
0.8587	High Similarity	NPC244356
0.8587	High Similarity	NPC291373
0.8587	High Similarity	NPC294263
0.8587	High Similarity	NPC86368
0.8587	High Similarity	NPC224060
0.8571	High Similarity	NPC113989
0.8571	High Similarity	NPC175628
0.8571	High Similarity	NPC120840
0.8571	High Similarity	NPC148414
0.8571	High Similarity	NPC111585
0.8557	High Similarity	NPC470310
0.8556	High Similarity	NPC211162
0.8556	High Similarity	NPC183374
0.8526	High Similarity	NPC474092
0.8526	High Similarity	NPC78427
0.8526	High Similarity	NPC119036
0.8526	High Similarity	NPC164349
0.8526	High Similarity	NPC16911
0.8523	High Similarity	NPC319909
0.8523	High Similarity	NPC74595
0.8523	High Similarity	NPC474482
0.8523	High Similarity	NPC475745
0.8523	High Similarity	NPC264665
0.8511	High Similarity	NPC13949
0.8511	High Similarity	NPC329910
0.8511	High Similarity	NPC234564
0.8495	Intermediate Similarity	NPC475118
0.8495	Intermediate Similarity	NPC469982
0.8488	Intermediate Similarity	NPC206735
0.8478	Intermediate Similarity	NPC250753
0.8478	Intermediate Similarity	NPC60755
0.8478	Intermediate Similarity	NPC285184
0.8478	Intermediate Similarity	NPC470590
0.8478	Intermediate Similarity	NPC228784
0.8478	Intermediate Similarity	NPC155120
0.8478	Intermediate Similarity	NPC324341
0.8478	Intermediate Similarity	NPC26888
0.8478	Intermediate Similarity	NPC966
0.8478	Intermediate Similarity	NPC288833
0.8478	Intermediate Similarity	NPC282616
0.8478	Intermediate Similarity	NPC77099
0.8462	Intermediate Similarity	NPC30522
0.8462	Intermediate Similarity	NPC474704
0.8462	Intermediate Similarity	NPC474570
0.8462	Intermediate Similarity	NPC471043
0.8462	Intermediate Similarity	NPC475921
0.8444	Intermediate Similarity	NPC252714
0.8438	Intermediate Similarity	NPC180733
0.8438	Intermediate Similarity	NPC287676
0.8438	Intermediate Similarity	NPC41971
0.8438	Intermediate Similarity	NPC37047
0.8427	Intermediate Similarity	NPC292553
0.8421	Intermediate Similarity	NPC469810
0.8409	Intermediate Similarity	NPC473742
0.8404	Intermediate Similarity	NPC470232
0.8404	Intermediate Similarity	NPC473648
0.8384	Intermediate Similarity	NPC265127
0.8372	Intermediate Similarity	NPC192744
0.837	Intermediate Similarity	NPC172361
0.837	Intermediate Similarity	NPC86372
0.837	Intermediate Similarity	NPC474728
0.8353	Intermediate Similarity	NPC68828
0.8351	Intermediate Similarity	NPC46848
0.8351	Intermediate Similarity	NPC473514
0.8351	Intermediate Similarity	NPC289148
0.8351	Intermediate Similarity	NPC163963
0.8351	Intermediate Similarity	NPC52899
0.8333	Intermediate Similarity	NPC11035
0.8333	Intermediate Similarity	NPC474793
0.8333	Intermediate Similarity	NPC471038
0.8333	Intermediate Similarity	NPC472738
0.8333	Intermediate Similarity	NPC98236
0.8333	Intermediate Similarity	NPC80590
0.8333	Intermediate Similarity	NPC187545
0.8333	Intermediate Similarity	NPC472505
0.8333	Intermediate Similarity	NPC269396
0.8316	Intermediate Similarity	NPC98874
0.8315	Intermediate Similarity	NPC299963
0.8315	Intermediate Similarity	NPC474233
0.8298	Intermediate Similarity	NPC159410
0.8298	Intermediate Similarity	NPC296164
0.8298	Intermediate Similarity	NPC74751
0.8298	Intermediate Similarity	NPC222047
0.8298	Intermediate Similarity	NPC470385
0.8298	Intermediate Similarity	NPC470386
0.8295	Intermediate Similarity	NPC289486
0.8295	Intermediate Similarity	NPC61107
0.828	Intermediate Similarity	NPC471588
0.828	Intermediate Similarity	NPC470230
0.828	Intermediate Similarity	NPC198242
0.828	Intermediate Similarity	NPC211403
0.828	Intermediate Similarity	NPC6255
0.8265	Intermediate Similarity	NPC286519
0.8265	Intermediate Similarity	NPC246736
0.8265	Intermediate Similarity	NPC475558
0.8265	Intermediate Similarity	NPC275990
0.8265	Intermediate Similarity	NPC88203
0.8265	Intermediate Similarity	NPC304832
0.8265	Intermediate Similarity	NPC473788
0.8265	Intermediate Similarity	NPC214946
0.8265	Intermediate Similarity	NPC76866
0.8265	Intermediate Similarity	NPC148628
0.8261	Intermediate Similarity	NPC293048
0.8261	Intermediate Similarity	NPC59263
0.8261	Intermediate Similarity	NPC130520
0.8261	Intermediate Similarity	NPC61543
0.8261	Intermediate Similarity	NPC77001
0.8261	Intermediate Similarity	NPC225585
0.8261	Intermediate Similarity	NPC116146
0.8261	Intermediate Similarity	NPC24772
0.8261	Intermediate Similarity	NPC270768
0.8261	Intermediate Similarity	NPC127689
0.8261	Intermediate Similarity	NPC121798
0.8261	Intermediate Similarity	NPC234346
0.8261	Intermediate Similarity	NPC263393
0.8261	Intermediate Similarity	NPC253618
0.8256	Intermediate Similarity	NPC63020
0.8247	Intermediate Similarity	NPC475156
0.8247	Intermediate Similarity	NPC473576
0.8242	Intermediate Similarity	NPC474684
0.8242	Intermediate Similarity	NPC46912
0.8242	Intermediate Similarity	NPC142361
0.8242	Intermediate Similarity	NPC162107
0.8242	Intermediate Similarity	NPC4643
0.8235	Intermediate Similarity	NPC246445
0.8229	Intermediate Similarity	NPC158347
0.8229	Intermediate Similarity	NPC476879
0.8229	Intermediate Similarity	NPC476878
0.8218	Intermediate Similarity	NPC88744
0.8211	Intermediate Similarity	NPC148523
0.8211	Intermediate Similarity	NPC184848
0.8211	Intermediate Similarity	NPC98639
0.8211	Intermediate Similarity	NPC69548
0.8211	Intermediate Similarity	NPC474727
0.8202	Intermediate Similarity	NPC245866
0.8202	Intermediate Similarity	NPC471036
0.8202	Intermediate Similarity	NPC291320

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 NPC471901 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	2027
0.2-0.3	4054
0.3-0.4	1948
0.4-0.5	478
0.5-0.6	191
0.6-0.7	183
0.7-0.8	78
0.8-0.85	1
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9318	High Similarity	NPD8035	Phase 2
0.9318	High Similarity	NPD8034	Phase 2
0.907	High Similarity	NPD7520	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD7748	Approved
0.8041	Intermediate Similarity	NPD7902	Approved
0.8023	Intermediate Similarity	NPD6117	Approved
0.8	Intermediate Similarity	NPD6399	Phase 3
0.7931	Intermediate Similarity	NPD6116	Phase 1
0.7895	Intermediate Similarity	NPD7515	Phase 2
0.7841	Intermediate Similarity	NPD6115	Approved
0.7841	Intermediate Similarity	NPD6697	Approved
0.7841	Intermediate Similarity	NPD6118	Approved
0.7841	Intermediate Similarity	NPD6114	Approved
0.7791	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD7900	Approved
0.767	Intermediate Similarity	NPD6675	Approved
0.767	Intermediate Similarity	NPD5739	Approved
0.767	Intermediate Similarity	NPD7128	Approved
0.767	Intermediate Similarity	NPD6402	Approved
0.76	Intermediate Similarity	NPD7638	Approved
0.7579	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD4786	Approved
0.7525	Intermediate Similarity	NPD7639	Approved
0.7525	Intermediate Similarity	NPD7640	Approved
0.7524	Intermediate Similarity	NPD6899	Approved
0.7524	Intermediate Similarity	NPD6881	Approved
0.7524	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD6083	Phase 2
0.75	Intermediate Similarity	NPD6084	Phase 2
0.75	Intermediate Similarity	NPD5328	Approved
0.7477	Intermediate Similarity	NPD8130	Phase 1
0.7455	Intermediate Similarity	NPD7115	Discovery
0.7453	Intermediate Similarity	NPD6372	Approved
0.7453	Intermediate Similarity	NPD6373	Approved
0.7429	Intermediate Similarity	NPD5697	Approved
0.7429	Intermediate Similarity	NPD5701	Approved
0.7419	Intermediate Similarity	NPD4788	Approved
0.7407	Intermediate Similarity	NPD8297	Approved
0.7396	Intermediate Similarity	NPD5737	Approved
0.7396	Intermediate Similarity	NPD6672	Approved
0.7383	Intermediate Similarity	NPD7290	Approved
0.7383	Intermediate Similarity	NPD6883	Approved
0.7383	Intermediate Similarity	NPD7102	Approved
0.7368	Intermediate Similarity	NPD6684	Approved
0.7368	Intermediate Similarity	NPD3618	Phase 1
0.7368	Intermediate Similarity	NPD7146	Approved
0.7368	Intermediate Similarity	NPD5330	Approved
0.7368	Intermediate Similarity	NPD7334	Approved
0.7368	Intermediate Similarity	NPD7521	Approved
0.7368	Intermediate Similarity	NPD6409	Approved
0.7356	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6079	Approved
0.7339	Intermediate Similarity	NPD8133	Approved
0.7315	Intermediate Similarity	NPD6869	Approved
0.7315	Intermediate Similarity	NPD6650	Approved
0.7315	Intermediate Similarity	NPD6847	Approved
0.7315	Intermediate Similarity	NPD6617	Approved
0.7315	Intermediate Similarity	NPD6649	Approved
0.7312	Intermediate Similarity	NPD3667	Approved
0.73	Intermediate Similarity	NPD5695	Phase 3
0.729	Intermediate Similarity	NPD6014	Approved
0.729	Intermediate Similarity	NPD6013	Approved
0.729	Intermediate Similarity	NPD6012	Approved
0.7283	Intermediate Similarity	NPD7525	Registered
0.7255	Intermediate Similarity	NPD5696	Approved
0.7248	Intermediate Similarity	NPD6882	Approved
0.7216	Intermediate Similarity	NPD6903	Approved
0.7196	Intermediate Similarity	NPD6011	Approved
0.7174	Intermediate Similarity	NPD7645	Phase 2
0.7172	Intermediate Similarity	NPD6411	Approved
0.7159	Intermediate Similarity	NPD6081	Approved
0.7159	Intermediate Similarity	NPD5777	Approved
0.7157	Intermediate Similarity	NPD4755	Approved
0.7156	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7736	Approved
0.7111	Intermediate Similarity	NPD3702	Approved
0.71	Intermediate Similarity	NPD4202	Approved
0.7059	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5222	Approved
0.7059	Intermediate Similarity	NPD5221	Approved
0.7059	Intermediate Similarity	NPD4697	Phase 3
0.7048	Intermediate Similarity	NPD7632	Discontinued
0.7019	Intermediate Similarity	NPD5286	Approved
0.7019	Intermediate Similarity	NPD4700	Approved
0.7019	Intermediate Similarity	NPD4696	Approved
0.7019	Intermediate Similarity	NPD5285	Approved
0.7011	Intermediate Similarity	NPD5360	Phase 3
0.7011	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6098	Approved
0.701	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7637	Suspended
0.6991	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5173	Approved
0.6979	Remote Similarity	NPD3666	Approved
0.6979	Remote Similarity	NPD3668	Phase 3
0.6979	Remote Similarity	NPD3133	Approved
0.6979	Remote Similarity	NPD3665	Phase 1
0.6977	Remote Similarity	NPD4224	Phase 2
0.697	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4753	Phase 2
0.697	Remote Similarity	NPD6101	Approved
0.697	Remote Similarity	NPD6673	Approved
0.697	Remote Similarity	NPD6080	Approved
0.697	Remote Similarity	NPD6904	Approved
0.6957	Remote Similarity	NPD6319	Approved
0.6923	Remote Similarity	NPD4225	Approved
0.6923	Remote Similarity	NPD3703	Phase 2
0.6923	Remote Similarity	NPD8328	Phase 3
0.6917	Remote Similarity	NPD7319	Approved
0.6903	Remote Similarity	NPD6274	Approved
0.6903	Remote Similarity	NPD6868	Approved
0.6891	Remote Similarity	NPD8293	Discontinued
0.6887	Remote Similarity	NPD5211	Phase 2
0.6887	Remote Similarity	NPD5225	Approved
0.6887	Remote Similarity	NPD5226	Approved
0.6887	Remote Similarity	NPD5224	Approved
0.6887	Remote Similarity	NPD4633	Approved
0.6881	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.687	Remote Similarity	NPD7100	Approved
0.687	Remote Similarity	NPD7101	Approved
0.6864	Remote Similarity	NPD7492	Approved
0.6854	Remote Similarity	NPD4245	Approved
0.6854	Remote Similarity	NPD4244	Approved
0.6854	Remote Similarity	NPD4789	Approved
0.6852	Remote Similarity	NPD6008	Approved
0.6822	Remote Similarity	NPD5174	Approved
0.6822	Remote Similarity	NPD5175	Approved
0.6818	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6054	Approved
0.681	Remote Similarity	NPD6059	Approved
0.6807	Remote Similarity	NPD6616	Approved
0.6807	Remote Similarity	NPD7507	Approved
0.6792	Remote Similarity	NPD5223	Approved
0.6789	Remote Similarity	NPD6412	Phase 2
0.6783	Remote Similarity	NPD6335	Approved
0.6771	Remote Similarity	NPD4223	Phase 3
0.6771	Remote Similarity	NPD4221	Approved
0.6768	Remote Similarity	NPD3573	Approved
0.6759	Remote Similarity	NPD5141	Approved
0.6757	Remote Similarity	NPD4634	Approved
0.6752	Remote Similarity	NPD6909	Approved
0.6752	Remote Similarity	NPD6908	Approved
0.675	Remote Similarity	NPD7078	Approved
0.6742	Remote Similarity	NPD3698	Phase 2
0.6742	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6942	Approved
0.6739	Remote Similarity	NPD7339	Approved
0.6735	Remote Similarity	NPD5329	Approved
0.6726	Remote Similarity	NPD4632	Approved
0.67	Remote Similarity	NPD5208	Approved
0.6699	Remote Similarity	NPD6001	Approved
0.6697	Remote Similarity	NPD4767	Approved
0.6697	Remote Similarity	NPD4768	Approved
0.6696	Remote Similarity	NPD6317	Approved
0.6695	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5693	Phase 1
0.6667	Remote Similarity	NPD6050	Approved
0.6667	Remote Similarity	NPD5281	Approved
0.6638	Remote Similarity	NPD6314	Approved
0.6638	Remote Similarity	NPD6313	Approved
0.6635	Remote Similarity	NPD4629	Approved
0.6635	Remote Similarity	NPD5210	Approved
0.6634	Remote Similarity	NPD6051	Approved
0.6634	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4197	Approved
0.661	Remote Similarity	NPD6016	Approved
0.661	Remote Similarity	NPD6015	Approved
0.6602	Remote Similarity	NPD5778	Approved
0.6602	Remote Similarity	NPD5779	Approved
0.6598	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4758	Discontinued
0.6577	Remote Similarity	NPD5128	Approved
0.6577	Remote Similarity	NPD4730	Approved
0.6577	Remote Similarity	NPD4729	Approved
0.6569	Remote Similarity	NPD5692	Phase 3
0.6555	Remote Similarity	NPD5988	Approved
0.6552	Remote Similarity	NPD6009	Approved
0.6542	Remote Similarity	NPD8418	Phase 2
0.6526	Remote Similarity	NPD3671	Phase 1
0.6526	Remote Similarity	NPD3617	Approved
0.6526	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5364	Discontinued
0.6525	Remote Similarity	NPD8377	Approved
0.6525	Remote Similarity	NPD8294	Approved
0.6518	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5694	Approved
0.65	Remote Similarity	NPD4689	Approved
0.65	Remote Similarity	NPD7604	Phase 2
0.65	Remote Similarity	NPD5205	Approved
0.65	Remote Similarity	NPD4688	Approved
0.65	Remote Similarity	NPD4138	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