NPASS Compound

Structure

CID229871 OpenBabel06191716022D 34 37 0 0 1 0 0 0 0 0999 V2000 -2.1474 -2.8474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7257 -2.0255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1195 -3.6660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4660 2.4064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3175 1.9147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6436 -0.9840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8215 1.4928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8516 0.4920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4651 -1.4223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8224 1.4234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2867 -0.0009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4652 -0.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4649 -0.4738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6969 -2.8458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0005 -1.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1993 -2.8469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6450 -2.8452 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6445 -1.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8224 -1.4228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2233 -3.6671 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8215 -1.4233 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6442 0.9486 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2869 0.9481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7248 -3.6677 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8218 -0.4748 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4657 1.4229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6439 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8221 -0.4743 0.0000 C 0 0 2 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 0.6979 -4.4879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6643 -1.9105 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1302 1.4345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1983 -4.4891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 2 17 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 9 13 1 0 0 0 0 9 19 1 0 0 0 0 10 14 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 28 1 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 18 1 0 0 0 0 15 21 1 0 0 0 0 16 20 1 0 0 0 0 16 22 1 0 0 0 0 17 25 1 0 0 0 0 18 3 1 6 0 0 0 18 19 1 0 0 0 0 19 20 2 0 0 0 0 20 29 1 0 0 0 0 21 25 1 0 0 0 0 21 31 1 6 0 0 0 22 26 1 0 0 0 0 22 32 1 6 0 0 0 23 27 1 0 0 0 0 23 28 1 6 0 0 0 24 27 1 0 0 0 0 24 33 2 0 0 0 0 25 34 1 1 0 0 0 26 28 1 1 0 0 0 26 30 1 0 0 0 0 28 6 1 6 0 0 0 29 30 1 1 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	520.462
LogP:	4.617
LogD:	3.873
LogS:	-4.792
# Rotatable Bonds:	5
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.455
Synthetic Accessibility Score:	5.176
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.175
MDCK Permeability:	1.3573321666626725e-05
Pgp-inhibitor:	0.968
Pgp-substrate:	0.13
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.896
30% Bioavailability (F30%):	0.205

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.567
Plasma Protein Binding (PPB):	89.30648040771484%
Volume Distribution (VD):	1.15
Pgp-substrate:	6.574089050292969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.512
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.941
CYP2C9-inhibitor:	0.09
CYP2C9-substrate:	0.184
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.837
CYP3A4-substrate:	0.784

ADMET: Excretion

Clearance (CL):	9.542
Half-life (T1/2):	0.194

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.263
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.801
Maximum Recommended Daily Dose:	0.891
Skin Sensitization:	0.077
Carcinogencity:	0.515
Eye Corrosion:	0.004
Eye Irritation:	0.018
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC229871

Natural Product ID:	NPC229871
*Common Name:**	25-Anhydroalisol A
IUPAC Name:	(5R,8S,9S,10S,11S,14R)-17-[(2R,4S,5S)-4,5-dihydroxy-6-methylhept-6-en-2-yl]-11-hydroxy-4,4,8,10,14-pentamethyl-1,2,5,6,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-3-one
Synonyms:
Standard InCHIKey:	WLNDANGOFVYODW-XCXJHVMUSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-17(2)25(34)21(31)15-18(3)19-9-13-29(7)20(19)16-22(32)26-28(6)12-11-24(33)27(4,5)23(28)10-14-30(26,29)8/h18,21-23,25-26,31-32,34H,1,9-16H2,2-8H3/t18-,21+,22+,23+,25+,26+,28+,29+,30+/m1/s1
SMILES:	CC(=C)[C@@H]([C@H](C[C@H](C1=C2C[C@H](O)[C@@H]3[C@]([C@]2(CC1)C)(C)CC[C@@H]1[C@]3(C)CCC(=O)C1(C)C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3121588
PubChem CID:	76314443
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
NPO14364.1	Alisma plantago-aquatica subsp. orientale	Subspecies	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3061	Alisma orientalis	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3061	Alisma orientalis	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14364.1	Alisma plantago-aquatica subsp. orientale	Subspecies	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10306	Alisma orienatale	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14364.1	Alisma plantago-aquatica subsp. orientale	Subspecies	Alismataceae	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
EC50	1
IC50	1

Activity Type	# Activity
Individual Protein	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	EC50	=	24090.0	nM	PMID[520670]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	600.0	nM	PMID[520669]

☑ 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 NPC229871 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	187
0.1-0.2	1231
0.2-0.3	4469
0.3-0.4	11964
0.4-0.5	11212
0.5-0.6	6043
0.6-0.7	5077
0.7-0.8	2273
0.8-0.85	213
0.85-0.9	20
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469319
0.9398	High Similarity	NPC473157
0.9294	High Similarity	NPC469317
0.9294	High Similarity	NPC469314
0.9294	High Similarity	NPC241875
0.9022	High Similarity	NPC473176
0.8876	High Similarity	NPC473167
0.8876	High Similarity	NPC473166
0.8864	High Similarity	NPC32830
0.8824	High Similarity	NPC86370
0.8791	High Similarity	NPC473170
0.8778	High Similarity	NPC198074
0.8778	High Similarity	NPC274046
0.8723	High Similarity	NPC476897
0.8696	High Similarity	NPC117133
0.8667	High Similarity	NPC155304
0.8621	High Similarity	NPC292553
0.8602	High Similarity	NPC474938
0.8602	High Similarity	NPC474785
0.8587	High Similarity	NPC37787
0.8587	High Similarity	NPC469329
0.8587	High Similarity	NPC473415
0.8587	High Similarity	NPC180557
0.8587	High Similarity	NPC30677
0.8571	High Similarity	NPC109305
0.8556	High Similarity	NPC126993
0.8556	High Similarity	NPC85173
0.8556	High Similarity	NPC48010
0.8539	High Similarity	NPC474677
0.8539	High Similarity	NPC193360
0.8523	High Similarity	NPC471737
0.8523	High Similarity	NPC472738
0.8511	High Similarity	NPC471784
0.8511	High Similarity	NPC303777
0.8506	High Similarity	NPC59453
0.8506	High Similarity	NPC221758
0.8488	Intermediate Similarity	NPC151519
0.8488	Intermediate Similarity	NPC212083
0.8478	Intermediate Similarity	NPC472976
0.8478	Intermediate Similarity	NPC87095
0.8478	Intermediate Similarity	NPC474690
0.8478	Intermediate Similarity	NPC473162
0.8478	Intermediate Similarity	NPC472977
0.8462	Intermediate Similarity	NPC212301
0.8462	Intermediate Similarity	NPC86266
0.8462	Intermediate Similarity	NPC110657
0.8462	Intermediate Similarity	NPC473998
0.8462	Intermediate Similarity	NPC189520
0.8444	Intermediate Similarity	NPC119416
0.8444	Intermediate Similarity	NPC77263
0.8444	Intermediate Similarity	NPC309603
0.8444	Intermediate Similarity	NPC31985
0.8444	Intermediate Similarity	NPC473999
0.8444	Intermediate Similarity	NPC250592
0.8444	Intermediate Similarity	NPC474245
0.8444	Intermediate Similarity	NPC1015
0.8438	Intermediate Similarity	NPC469316
0.8427	Intermediate Similarity	NPC90652
0.8427	Intermediate Similarity	NPC475740
0.8427	Intermediate Similarity	NPC138756
0.8427	Intermediate Similarity	NPC73064
0.8427	Intermediate Similarity	NPC4643
0.8409	Intermediate Similarity	NPC197823
0.8409	Intermediate Similarity	NPC470574
0.8409	Intermediate Similarity	NPC471224
0.8409	Intermediate Similarity	NPC133954
0.8391	Intermediate Similarity	NPC472743
0.8391	Intermediate Similarity	NPC475726
0.8387	Intermediate Similarity	NPC53565
0.837	Intermediate Similarity	NPC170220
0.837	Intermediate Similarity	NPC474806
0.837	Intermediate Similarity	NPC141497
0.837	Intermediate Similarity	NPC107674
0.837	Intermediate Similarity	NPC133579
0.837	Intermediate Similarity	NPC12722
0.837	Intermediate Similarity	NPC474736
0.8352	Intermediate Similarity	NPC469400
0.8333	Intermediate Similarity	NPC471722
0.8333	Intermediate Similarity	NPC16377
0.8333	Intermediate Similarity	NPC470417
0.8333	Intermediate Similarity	NPC242864
0.8315	Intermediate Similarity	NPC145879
0.8315	Intermediate Similarity	NPC72133
0.8315	Intermediate Similarity	NPC31564
0.8315	Intermediate Similarity	NPC469994
0.8315	Intermediate Similarity	NPC475862
0.8315	Intermediate Similarity	NPC51014
0.8315	Intermediate Similarity	NPC470955
0.8315	Intermediate Similarity	NPC474733
0.8315	Intermediate Similarity	NPC322159
0.8315	Intermediate Similarity	NPC213412
0.8315	Intermediate Similarity	NPC158393
0.8315	Intermediate Similarity	NPC474732
0.8315	Intermediate Similarity	NPC74363
0.8315	Intermediate Similarity	NPC474778
0.8298	Intermediate Similarity	NPC235053
0.8298	Intermediate Similarity	NPC471777
0.8295	Intermediate Similarity	NPC180834
0.8295	Intermediate Similarity	NPC227132
0.8295	Intermediate Similarity	NPC475745
0.8295	Intermediate Similarity	NPC474482
0.828	Intermediate Similarity	NPC245972
0.828	Intermediate Similarity	NPC8993
0.828	Intermediate Similarity	NPC299100
0.828	Intermediate Similarity	NPC292793
0.828	Intermediate Similarity	NPC49670
0.828	Intermediate Similarity	NPC196485
0.828	Intermediate Similarity	NPC240617
0.8276	Intermediate Similarity	NPC477858
0.8276	Intermediate Similarity	NPC145143
0.8276	Intermediate Similarity	NPC48362
0.8261	Intermediate Similarity	NPC272746
0.8261	Intermediate Similarity	NPC235884
0.8261	Intermediate Similarity	NPC300351
0.8261	Intermediate Similarity	NPC52021
0.8261	Intermediate Similarity	NPC306541
0.8261	Intermediate Similarity	NPC475806
0.8261	Intermediate Similarity	NPC71074
0.8261	Intermediate Similarity	NPC63748
0.8261	Intermediate Similarity	NPC25299
0.8261	Intermediate Similarity	NPC84319
0.8261	Intermediate Similarity	NPC472149
0.8261	Intermediate Similarity	NPC233116
0.8247	Intermediate Similarity	NPC477915
0.8247	Intermediate Similarity	NPC473424
0.8242	Intermediate Similarity	NPC474704
0.8242	Intermediate Similarity	NPC274330
0.8242	Intermediate Similarity	NPC122116
0.8242	Intermediate Similarity	NPC143232
0.8242	Intermediate Similarity	NPC220498
0.8242	Intermediate Similarity	NPC198664
0.8242	Intermediate Similarity	NPC475921
0.8229	Intermediate Similarity	NPC110149
0.8222	Intermediate Similarity	NPC141292
0.8222	Intermediate Similarity	NPC474684
0.8222	Intermediate Similarity	NPC317590
0.8222	Intermediate Similarity	NPC58063
0.8222	Intermediate Similarity	NPC469322
0.8222	Intermediate Similarity	NPC142361
0.8222	Intermediate Similarity	NPC477926
0.8211	Intermediate Similarity	NPC320306
0.8211	Intermediate Similarity	NPC190554
0.8202	Intermediate Similarity	NPC474083
0.8202	Intermediate Similarity	NPC76518
0.8202	Intermediate Similarity	NPC274724
0.8191	Intermediate Similarity	NPC271195
0.8191	Intermediate Similarity	NPC96916
0.8191	Intermediate Similarity	NPC32118
0.8191	Intermediate Similarity	NPC180950
0.8182	Intermediate Similarity	NPC149047
0.8182	Intermediate Similarity	NPC215893
0.8182	Intermediate Similarity	NPC166607
0.8172	Intermediate Similarity	NPC74855
0.8172	Intermediate Similarity	NPC472496
0.8172	Intermediate Similarity	NPC69454
0.8172	Intermediate Similarity	NPC475255
0.8172	Intermediate Similarity	NPC136313
0.8172	Intermediate Similarity	NPC307335
0.8172	Intermediate Similarity	NPC275809
0.8163	Intermediate Similarity	NPC475050
0.8163	Intermediate Similarity	NPC324001
0.8163	Intermediate Similarity	NPC471005
0.8161	Intermediate Similarity	NPC474484
0.8161	Intermediate Similarity	NPC103754
0.8161	Intermediate Similarity	NPC328264
0.8152	Intermediate Similarity	NPC111110
0.8152	Intermediate Similarity	NPC136801
0.8152	Intermediate Similarity	NPC126369
0.8152	Intermediate Similarity	NPC49320
0.8152	Intermediate Similarity	NPC291028
0.8152	Intermediate Similarity	NPC470589
0.814	Intermediate Similarity	NPC476812
0.814	Intermediate Similarity	NPC472463
0.8132	Intermediate Similarity	NPC471724
0.8132	Intermediate Similarity	NPC310752
0.8132	Intermediate Similarity	NPC328313
0.8132	Intermediate Similarity	NPC473242
0.8132	Intermediate Similarity	NPC470629
0.8132	Intermediate Similarity	NPC53911
0.8132	Intermediate Similarity	NPC182797
0.8132	Intermediate Similarity	NPC290690
0.8132	Intermediate Similarity	NPC474719
0.8132	Intermediate Similarity	NPC292491
0.8132	Intermediate Similarity	NPC131470
0.8132	Intermediate Similarity	NPC328539
0.8132	Intermediate Similarity	NPC17733
0.8132	Intermediate Similarity	NPC52169
0.8132	Intermediate Similarity	NPC206060
0.8132	Intermediate Similarity	NPC474512
0.8132	Intermediate Similarity	NPC67872
0.8132	Intermediate Similarity	NPC472802
0.8132	Intermediate Similarity	NPC181225
0.8132	Intermediate Similarity	NPC143767
0.8132	Intermediate Similarity	NPC230387
0.8118	Intermediate Similarity	NPC472746
0.8118	Intermediate Similarity	NPC149249
0.8111	Intermediate Similarity	NPC28252
0.8111	Intermediate Similarity	NPC56588
0.8111	Intermediate Similarity	NPC477579
0.8111	Intermediate Similarity	NPC187545

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 NPC229871 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1577
0.2-0.3	3812
0.3-0.4	2404
0.4-0.5	729
0.5-0.6	191
0.6-0.7	201
0.7-0.8	69
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8506	High Similarity	NPD4786	Approved
0.8488	Intermediate Similarity	NPD3667	Approved
0.8315	Intermediate Similarity	NPD3618	Phase 1
0.8242	Intermediate Similarity	NPD5328	Approved
0.8065	Intermediate Similarity	NPD6079	Approved
0.8065	Intermediate Similarity	NPD7515	Phase 2
0.8	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD3665	Phase 1
0.7889	Intermediate Similarity	NPD3668	Phase 3
0.7889	Intermediate Similarity	NPD3666	Approved
0.7889	Intermediate Similarity	NPD3133	Approved
0.7841	Intermediate Similarity	NPD7525	Registered
0.7789	Intermediate Similarity	NPD4202	Approved
0.7789	Intermediate Similarity	NPD6399	Phase 3
0.7732	Intermediate Similarity	NPD4697	Phase 3
0.7732	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD5222	Approved
0.7732	Intermediate Similarity	NPD5221	Approved
0.7708	Intermediate Similarity	NPD7748	Approved
0.77	Intermediate Similarity	NPD5211	Phase 2
0.7677	Intermediate Similarity	NPD7640	Approved
0.7677	Intermediate Similarity	NPD7639	Approved
0.7653	Intermediate Similarity	NPD4755	Approved
0.7653	Intermediate Similarity	NPD5173	Approved
0.7582	Intermediate Similarity	NPD4788	Approved
0.7576	Intermediate Similarity	NPD7638	Approved
0.7549	Intermediate Similarity	NPD5141	Approved
0.7529	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5286	Approved
0.75	Intermediate Similarity	NPD4700	Approved
0.75	Intermediate Similarity	NPD8035	Phase 2
0.75	Intermediate Similarity	NPD8034	Phase 2
0.75	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4696	Approved
0.75	Intermediate Similarity	NPD5285	Approved
0.7475	Intermediate Similarity	NPD7902	Approved
0.7474	Intermediate Similarity	NPD4753	Phase 2
0.7471	Intermediate Similarity	NPD6942	Approved
0.7471	Intermediate Similarity	NPD7339	Approved
0.7431	Intermediate Similarity	NPD7115	Discovery
0.7426	Intermediate Similarity	NPD5223	Approved
0.7386	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6117	Approved
0.7353	Intermediate Similarity	NPD5224	Approved
0.7353	Intermediate Similarity	NPD5225	Approved
0.7353	Intermediate Similarity	NPD5226	Approved
0.7353	Intermediate Similarity	NPD4633	Approved
0.734	Intermediate Similarity	NPD4519	Discontinued
0.734	Intermediate Similarity	NPD5279	Phase 3
0.734	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD4623	Approved
0.7333	Intermediate Similarity	NPD7645	Phase 2
0.7308	Intermediate Similarity	NPD7128	Approved
0.7308	Intermediate Similarity	NPD5739	Approved
0.7308	Intermediate Similarity	NPD6675	Approved
0.7308	Intermediate Similarity	NPD6402	Approved
0.7303	Intermediate Similarity	NPD6116	Phase 1
0.7283	Intermediate Similarity	NPD4221	Approved
0.7283	Intermediate Similarity	NPD4223	Phase 3
0.7282	Intermediate Similarity	NPD4754	Approved
0.7282	Intermediate Similarity	NPD5175	Approved
0.7282	Intermediate Similarity	NPD5174	Approved
0.7273	Intermediate Similarity	NPD3703	Phase 2
0.7253	Intermediate Similarity	NPD4695	Discontinued
0.7234	Intermediate Similarity	NPD5329	Approved
0.7228	Intermediate Similarity	NPD4225	Approved
0.7222	Intermediate Similarity	NPD6118	Approved
0.7222	Intermediate Similarity	NPD3617	Approved
0.7222	Intermediate Similarity	NPD6115	Approved
0.7222	Intermediate Similarity	NPD6114	Approved
0.7222	Intermediate Similarity	NPD6697	Approved
0.7209	Intermediate Similarity	NPD4245	Approved
0.7209	Intermediate Similarity	NPD4244	Approved
0.7196	Intermediate Similarity	NPD4634	Approved
0.7191	Intermediate Similarity	NPD6933	Approved
0.7188	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7632	Discontinued
0.7172	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7900	Approved
0.717	Intermediate Similarity	NPD7320	Approved
0.717	Intermediate Similarity	NPD6881	Approved
0.717	Intermediate Similarity	NPD6899	Approved
0.7159	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7146	Approved
0.7158	Intermediate Similarity	NPD7521	Approved
0.7158	Intermediate Similarity	NPD7334	Approved
0.7158	Intermediate Similarity	NPD6409	Approved
0.7158	Intermediate Similarity	NPD6684	Approved
0.7158	Intermediate Similarity	NPD5330	Approved
0.7143	Intermediate Similarity	NPD4767	Approved
0.7143	Intermediate Similarity	NPD4768	Approved
0.7129	Intermediate Similarity	NPD6084	Phase 2
0.7129	Intermediate Similarity	NPD6083	Phase 2
0.7128	Intermediate Similarity	NPD4197	Approved
0.7103	Intermediate Similarity	NPD6372	Approved
0.7103	Intermediate Similarity	NPD6373	Approved
0.71	Intermediate Similarity	NPD4629	Approved
0.71	Intermediate Similarity	NPD5210	Approved
0.7093	Intermediate Similarity	NPD3698	Phase 2
0.7075	Intermediate Similarity	NPD5697	Approved
0.7075	Intermediate Similarity	NPD6412	Phase 2
0.7075	Intermediate Similarity	NPD5701	Approved
0.7064	Intermediate Similarity	NPD8297	Approved
0.7037	Intermediate Similarity	NPD6883	Approved
0.7037	Intermediate Similarity	NPD7290	Approved
0.7037	Intermediate Similarity	NPD7102	Approved
0.7033	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4789	Approved
0.701	Intermediate Similarity	NPD5737	Approved
0.701	Intermediate Similarity	NPD6903	Approved
0.701	Intermediate Similarity	NPD6672	Approved
0.7009	Intermediate Similarity	NPD4729	Approved
0.7009	Intermediate Similarity	NPD4730	Approved
0.7009	Intermediate Similarity	NPD6011	Approved
0.7009	Intermediate Similarity	NPD5128	Approved
0.7009	Intermediate Similarity	NPD5168	Approved
0.7	Intermediate Similarity	NPD4632	Approved
0.6979	Remote Similarity	NPD4138	Approved
0.6979	Remote Similarity	NPD5205	Approved
0.6979	Remote Similarity	NPD4693	Phase 3
0.6979	Remote Similarity	NPD4690	Approved
0.6979	Remote Similarity	NPD4689	Approved
0.6979	Remote Similarity	NPD4688	Approved
0.6977	Remote Similarity	NPD5360	Phase 3
0.6977	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD8130	Phase 1
0.6972	Remote Similarity	NPD6617	Approved
0.6972	Remote Similarity	NPD6649	Approved
0.6972	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6847	Approved
0.6972	Remote Similarity	NPD6869	Approved
0.6972	Remote Similarity	NPD6650	Approved
0.6966	Remote Similarity	NPD6926	Approved
0.6966	Remote Similarity	NPD6924	Approved
0.6957	Remote Similarity	NPD6929	Approved
0.6944	Remote Similarity	NPD6012	Approved
0.6944	Remote Similarity	NPD6013	Approved
0.6944	Remote Similarity	NPD6014	Approved
0.6939	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6882	Approved
0.6907	Remote Similarity	NPD7524	Approved
0.6907	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6930	Phase 2
0.6882	Remote Similarity	NPD7509	Discontinued
0.6882	Remote Similarity	NPD6931	Approved
0.6881	Remote Similarity	NPD5250	Approved
0.6881	Remote Similarity	NPD5247	Approved
0.6881	Remote Similarity	NPD5135	Approved
0.6881	Remote Similarity	NPD5169	Approved
0.6881	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5249	Phase 3
0.6881	Remote Similarity	NPD5248	Approved
0.6881	Remote Similarity	NPD5251	Approved
0.6848	Remote Similarity	NPD3671	Phase 1
0.6848	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5362	Discontinued
0.6842	Remote Similarity	NPD6695	Phase 3
0.6824	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5215	Approved
0.6818	Remote Similarity	NPD5217	Approved
0.6818	Remote Similarity	NPD5216	Approved
0.6818	Remote Similarity	NPD5127	Approved
0.6809	Remote Similarity	NPD4692	Approved
0.6809	Remote Similarity	NPD4139	Approved
0.6804	Remote Similarity	NPD5690	Phase 2
0.6804	Remote Similarity	NPD4694	Approved
0.6804	Remote Similarity	NPD5280	Approved
0.68	Remote Similarity	NPD6411	Approved
0.6789	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5695	Phase 3
0.6742	Remote Similarity	NPD7152	Approved
0.6742	Remote Similarity	NPD7151	Approved
0.6742	Remote Similarity	NPD7150	Approved
0.6739	Remote Similarity	NPD6925	Approved
0.6739	Remote Similarity	NPD5776	Phase 2
0.6737	Remote Similarity	NPD4270	Approved
0.6737	Remote Similarity	NPD4269	Approved
0.6731	Remote Similarity	NPD5696	Approved
0.6726	Remote Similarity	NPD6868	Approved
0.6705	Remote Similarity	NPD6923	Approved
0.6705	Remote Similarity	NPD6922	Approved
0.6705	Remote Similarity	NPD4137	Phase 3
0.6703	Remote Similarity	NPD8264	Approved
0.6702	Remote Similarity	NPD7332	Phase 2
0.6702	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4748	Discontinued
0.6701	Remote Similarity	NPD1696	Phase 3
0.6697	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD7145	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD7154	Phase 3
0.6639	Remote Similarity	NPD7507	Approved
0.6638	Remote Similarity	NPD6059	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