NPASS Compound

Structure

NPC214279 OpenBabel07101718192D 38 43 0 0 1 0 0 0 0 0999 V2000 4.4108 1.4880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9005 -0.0191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3770 1.3723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5846 2.7447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2810 1.7707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7706 0.2636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1693 1.8298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3770 3.2021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0696 -2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2472 -1.0274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3770 0.4574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5846 1.8298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2206 0.5931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5846 1.8298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9609 1.1585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1693 2.7447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9645 -1.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3770 1.3723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4574 -1.4079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6351 -0.3475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5846 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7923 1.3723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7402 -0.5378 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7402 -0.5378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7923 0.4574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4574 -1.4079 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7923 1.3723 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7923 0.4574 0.0000 C 0 0 0 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 6.8310 1.4413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9616 3.2021 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5767 -2.5775 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1693 1.8298 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9178 0.5226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5846 -0.9149 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9952 -2.1480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3770 -0.4574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.8298 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 1 13 2 0 0 0 0 2 6 2 0 0 0 0 2 13 1 0 0 0 0 3 7 1 0 0 0 0 3 14 2 0 0 0 0 4 8 2 0 0 0 0 4 14 1 0 0 0 0 5 15 2 0 0 0 0 6 15 1 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 9 19 1 0 0 0 0 10 17 1 0 0 0 0 10 20 2 0 0 0 0 11 18 2 0 0 0 0 11 21 1 0 0 0 0 12 18 1 0 0 0 0 12 22 2 0 0 0 0 13 23 1 0 0 0 0 15 30 1 0 0 0 0 16 31 1 0 0 0 0 17 32 1 0 0 0 0 18 33 1 0 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 20 24 1 0 0 0 0 20 34 1 0 0 0 0 21 25 2 0 0 0 0 21 35 1 0 0 0 0 22 25 1 0 0 0 0 22 38 1 0 0 0 0 23 26 1 0 0 0 0 23 29 1 6 0 0 0 25 29 1 0 0 0 0 26 36 1 1 0 0 0 27 14 1 1 0 0 0 27 28 1 0 0 0 0 27 38 1 0 0 0 0 28 29 1 0 0 0 0 28 37 2 0 0 0 0 29 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	514.13
Volume:	503.639
LogP:	2.368
LogD:	1.993
LogS:	-3.898
# Rotatable Bonds:	2
TPSA:	167.91
# H-Bond Aceptor:	9
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.211
Synthetic Accessibility Score:	4.753
Fsp3:	0.138
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.323
MDCK Permeability:	4.247354354447452e-06
Pgp-inhibitor:	0.191
Pgp-substrate:	0.095
Human Intestinal Absorption (HIA):	0.474
20% Bioavailability (F20%):	0.964
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	96.3696060180664%
Volume Distribution (VD):	0.653
Pgp-substrate:	3.2332677841186523%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.109
CYP2C19-inhibitor:	0.544
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.845
CYP2C9-substrate:	0.985
CYP2D6-inhibitor:	0.381
CYP2D6-substrate:	0.555
CYP3A4-inhibitor:	0.795
CYP3A4-substrate:	0.589

ADMET: Excretion

Clearance (CL):	12.964
Half-life (T1/2):	0.841

ADMET: Toxicity

hERG Blockers:	0.102
Human Hepatotoxicity (H-HT):	0.222
Drug-inuced Liver Injury (DILI):	0.914
AMES Toxicity:	0.23
Rat Oral Acute Toxicity:	0.677
Maximum Recommended Daily Dose:	0.597
Skin Sensitization:	0.95
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.883
Respiratory Toxicity:	0.042

Download Data

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

Natural Product: NPC214279

Natural Product ID:	NPC214279
*Common Name:**	Yuccaone A
IUPAC Name:	(1R,2S,2'R,3R)-1,4,5',6,7'-pentahydroxy-2,2'-bis(4-hydroxyphenyl)spiro[1,2-dihydroindene-3,4'-chromene]-3'-one
Synonyms:
Standard InCHIKey:	SRCVSQMUWRYDDK-GOJGNYKUSA-N
Standard InCHI:	InChI=1S/C29H22O9/c30-15-5-1-13(2-6-15)23-26(36)19-9-17(32)10-20(34)24(19)29(23)25-21(35)11-18(33)12-22(25)38-27(28(29)37)14-3-7-16(31)8-4-14/h1-12,23,26-27,30-36H/t23-,26+,27-,29-/m1/s1
SMILES:	c1cc(ccc1[C@@H]1[C@H](c2cc(cc(c2[C@]21c1c(cc(cc1O[C@H](c1ccc(cc1)O)C2=O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516591
PubChem CID:	44559531
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO1943	Yucca schidigera	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757713]
NPO1943	Yucca schidigera	Species	Asparagaceae	Eukaryota	bark	n.a.	n.a.	PMID[15165156]
NPO1943	Yucca schidigera	Species	Asparagaceae	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
Others	3

Activity Type	# Activity
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	1.037	mM	PMID[564752]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	40.6	%	PMID[564752]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	43.4	%	PMID[564752]

☑ 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 NPC214279 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	438
0.1-0.2	1738
0.2-0.3	3424
0.3-0.4	8684
0.4-0.5	10383
0.5-0.6	4049
0.6-0.7	7059
0.7-0.8	6692
0.8-0.85	223
0.85-0.9	6
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8554	High Similarity	NPC290160
0.8537	High Similarity	NPC295090
0.8529	High Similarity	NPC470333
0.8528	High Similarity	NPC166116
0.8528	High Similarity	NPC55463
0.8466	Intermediate Similarity	NPC258474
0.8466	Intermediate Similarity	NPC201227
0.8443	Intermediate Similarity	NPC63438
0.8439	Intermediate Similarity	NPC70318
0.8434	Intermediate Similarity	NPC312273
0.8434	Intermediate Similarity	NPC301256
0.8434	Intermediate Similarity	NPC90822
0.8415	Intermediate Similarity	NPC198489
0.8415	Intermediate Similarity	NPC69531
0.8415	Intermediate Similarity	NPC61112
0.8415	Intermediate Similarity	NPC32867
0.8415	Intermediate Similarity	NPC309648
0.8393	Intermediate Similarity	NPC474591
0.8383	Intermediate Similarity	NPC473012
0.8383	Intermediate Similarity	NPC473011
0.8375	Intermediate Similarity	NPC17101
0.8375	Intermediate Similarity	NPC77903
0.8373	Intermediate Similarity	NPC184326
0.8373	Intermediate Similarity	NPC292863
0.8364	Intermediate Similarity	NPC271741
0.8364	Intermediate Similarity	NPC475184
0.8364	Intermediate Similarity	NPC287789
0.8363	Intermediate Similarity	NPC186847
0.8363	Intermediate Similarity	NPC472454
0.8363	Intermediate Similarity	NPC257667
0.8353	Intermediate Similarity	NPC107627
0.8343	Intermediate Similarity	NPC82330
0.8333	Intermediate Similarity	NPC473009
0.8323	Intermediate Similarity	NPC106328
0.8323	Intermediate Similarity	NPC137232
0.8323	Intermediate Similarity	NPC139540
0.8323	Intermediate Similarity	NPC35150
0.8323	Intermediate Similarity	NPC177100
0.8323	Intermediate Similarity	NPC18380
0.8313	Intermediate Similarity	NPC195167
0.8313	Intermediate Similarity	NPC123544
0.8293	Intermediate Similarity	NPC303950
0.8284	Intermediate Similarity	NPC473010
0.8274	Intermediate Similarity	NPC261896
0.8274	Intermediate Similarity	NPC15374
0.8253	Intermediate Similarity	NPC257166
0.8242	Intermediate Similarity	NPC134171
0.8242	Intermediate Similarity	NPC182555
0.8242	Intermediate Similarity	NPC300668
0.8242	Intermediate Similarity	NPC66441
0.8239	Intermediate Similarity	NPC470332
0.8235	Intermediate Similarity	NPC224851
0.8235	Intermediate Similarity	NPC320741
0.8235	Intermediate Similarity	NPC171985
0.8232	Intermediate Similarity	NPC174086
0.8232	Intermediate Similarity	NPC474843
0.8217	Intermediate Similarity	NPC213607
0.8217	Intermediate Similarity	NPC174787
0.8217	Intermediate Similarity	NPC182509
0.8214	Intermediate Similarity	NPC186228
0.8204	Intermediate Similarity	NPC51247
0.8204	Intermediate Similarity	NPC15815
0.8204	Intermediate Similarity	NPC472617
0.8198	Intermediate Similarity	NPC91043
0.8194	Intermediate Similarity	NPC11727
0.8194	Intermediate Similarity	NPC15109
0.8182	Intermediate Similarity	NPC121568
0.8182	Intermediate Similarity	NPC473365
0.8176	Intermediate Similarity	NPC469664
0.8155	Intermediate Similarity	NPC310399
0.8155	Intermediate Similarity	NPC472618
0.8155	Intermediate Similarity	NPC73422
0.815	Intermediate Similarity	NPC477529
0.8144	Intermediate Similarity	NPC1796
0.814	Intermediate Similarity	NPC286074
0.814	Intermediate Similarity	NPC54903
0.8133	Intermediate Similarity	NPC254351
0.8129	Intermediate Similarity	NPC120857
0.8129	Intermediate Similarity	NPC17274
0.8129	Intermediate Similarity	NPC85047
0.8129	Intermediate Similarity	NPC251336
0.8125	Intermediate Similarity	NPC120102
0.8118	Intermediate Similarity	NPC38591
0.8118	Intermediate Similarity	NPC469395
0.8114	Intermediate Similarity	NPC272656
0.8107	Intermediate Similarity	NPC96031
0.8107	Intermediate Similarity	NPC472153
0.8098	Intermediate Similarity	NPC122980
0.8098	Intermediate Similarity	NPC177172
0.8098	Intermediate Similarity	NPC180605
0.8098	Intermediate Similarity	NPC107862
0.8098	Intermediate Similarity	NPC122894
0.8098	Intermediate Similarity	NPC148516
0.8095	Intermediate Similarity	NPC18699
0.8095	Intermediate Similarity	NPC226287
0.8095	Intermediate Similarity	NPC105584
0.8095	Intermediate Similarity	NPC7543
0.8095	Intermediate Similarity	NPC209473
0.8095	Intermediate Similarity	NPC472156
0.8095	Intermediate Similarity	NPC94220
0.8095	Intermediate Similarity	NPC24339
0.8095	Intermediate Similarity	NPC98083
0.8095	Intermediate Similarity	NPC51760
0.8095	Intermediate Similarity	NPC329743
0.8095	Intermediate Similarity	NPC55443
0.8095	Intermediate Similarity	NPC166456
0.8092	Intermediate Similarity	NPC279209
0.8092	Intermediate Similarity	NPC8704
0.8092	Intermediate Similarity	NPC287884
0.8092	Intermediate Similarity	NPC102277
0.8084	Intermediate Similarity	NPC165483
0.8084	Intermediate Similarity	NPC192587
0.8081	Intermediate Similarity	NPC167231
0.8081	Intermediate Similarity	NPC260266
0.8081	Intermediate Similarity	NPC215802
0.8072	Intermediate Similarity	NPC20907
0.8072	Intermediate Similarity	NPC244250
0.807	Intermediate Similarity	NPC36916
0.807	Intermediate Similarity	NPC36
0.807	Intermediate Similarity	NPC58223
0.807	Intermediate Similarity	NPC7688
0.807	Intermediate Similarity	NPC7154
0.807	Intermediate Similarity	NPC72787
0.807	Intermediate Similarity	NPC314653
0.807	Intermediate Similarity	NPC316262
0.807	Intermediate Similarity	NPC125039
0.8068	Intermediate Similarity	NPC475783
0.8061	Intermediate Similarity	NPC120633
0.8061	Intermediate Similarity	NPC473018
0.8059	Intermediate Similarity	NPC219927
0.8059	Intermediate Similarity	NPC477841
0.8059	Intermediate Similarity	NPC326278
0.8049	Intermediate Similarity	NPC471114
0.8049	Intermediate Similarity	NPC3642
0.8049	Intermediate Similarity	NPC218801
0.8047	Intermediate Similarity	NPC226462
0.8047	Intermediate Similarity	NPC186325
0.8047	Intermediate Similarity	NPC98023
0.8047	Intermediate Similarity	NPC195136
0.8047	Intermediate Similarity	NPC42965
0.8046	Intermediate Similarity	NPC118128
0.8037	Intermediate Similarity	NPC259632
0.8036	Intermediate Similarity	NPC208258
0.8036	Intermediate Similarity	NPC323627
0.8036	Intermediate Similarity	NPC318527
0.8036	Intermediate Similarity	NPC324358
0.8036	Intermediate Similarity	NPC322459
0.8035	Intermediate Similarity	NPC41494
0.8035	Intermediate Similarity	NPC186100
0.8035	Intermediate Similarity	NPC20734
0.8035	Intermediate Similarity	NPC300307
0.8035	Intermediate Similarity	NPC53252
0.8035	Intermediate Similarity	NPC216403
0.8025	Intermediate Similarity	NPC311144
0.8025	Intermediate Similarity	NPC141717
0.8024	Intermediate Similarity	NPC79375
0.8024	Intermediate Similarity	NPC37253
0.8023	Intermediate Similarity	NPC477517
0.8023	Intermediate Similarity	NPC9309
0.8023	Intermediate Similarity	NPC244903
0.8012	Intermediate Similarity	NPC78324
0.8012	Intermediate Similarity	NPC120677
0.8012	Intermediate Similarity	NPC74371
0.8012	Intermediate Similarity	NPC39154
0.8012	Intermediate Similarity	NPC15659
0.8012	Intermediate Similarity	NPC327694
0.8012	Intermediate Similarity	NPC115601
0.8012	Intermediate Similarity	NPC208011
0.8012	Intermediate Similarity	NPC476295
0.8012	Intermediate Similarity	NPC304894
0.8	Intermediate Similarity	NPC157081
0.8	Intermediate Similarity	NPC189552
0.8	Intermediate Similarity	NPC155754
0.8	Intermediate Similarity	NPC105073
0.8	Intermediate Similarity	NPC109061
0.8	Intermediate Similarity	NPC90336
0.8	Intermediate Similarity	NPC224528
0.8	Intermediate Similarity	NPC124747
0.8	Intermediate Similarity	NPC233886
0.8	Intermediate Similarity	NPC469393
0.8	Intermediate Similarity	NPC273467
0.7989	Intermediate Similarity	NPC313717
0.7989	Intermediate Similarity	NPC193698
0.7989	Intermediate Similarity	NPC315306
0.7988	Intermediate Similarity	NPC4950
0.7988	Intermediate Similarity	NPC186113
0.7988	Intermediate Similarity	NPC177650
0.7988	Intermediate Similarity	NPC324736
0.7988	Intermediate Similarity	NPC218569
0.7977	Intermediate Similarity	NPC476306
0.7977	Intermediate Similarity	NPC295082
0.7976	Intermediate Similarity	NPC164244
0.7976	Intermediate Similarity	NPC78492
0.7976	Intermediate Similarity	NPC208152
0.7976	Intermediate Similarity	NPC137100
0.7975	Intermediate Similarity	NPC202112
0.7975	Intermediate Similarity	NPC51513
0.7975	Intermediate Similarity	NPC299011
0.7975	Intermediate Similarity	NPC223592
0.7966	Intermediate Similarity	NPC470334

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 NPC214279 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	943
0.2-0.3	1727
0.3-0.4	2690
0.4-0.5	1895
0.5-0.6	966
0.6-0.7	418
0.7-0.8	104
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.825	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD6959	Discontinued
0.807	Intermediate Similarity	NPD6166	Phase 2
0.807	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD3787	Discontinued
0.7917	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7199	Phase 2
0.787	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6099	Approved
0.7862	Intermediate Similarity	NPD6100	Approved
0.7742	Intermediate Similarity	NPD4908	Phase 1
0.7719	Intermediate Similarity	NPD3749	Approved
0.7702	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD4380	Phase 2
0.767	Intermediate Similarity	NPD3751	Discontinued
0.7657	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1549	Phase 2
0.7651	Intermediate Similarity	NPD6273	Approved
0.7647	Intermediate Similarity	NPD7819	Suspended
0.7647	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6797	Phase 2
0.7627	Intermediate Similarity	NPD5844	Phase 1
0.7627	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7075	Discontinued
0.7598	Intermediate Similarity	NPD7251	Discontinued
0.7588	Intermediate Similarity	NPD1934	Approved
0.7564	Intermediate Similarity	NPD2861	Phase 2
0.7561	Intermediate Similarity	NPD3750	Approved
0.7558	Intermediate Similarity	NPD3882	Suspended
0.7556	Intermediate Similarity	NPD7808	Phase 3
0.7556	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7229	Phase 3
0.7529	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD5402	Approved
0.7486	Intermediate Similarity	NPD7074	Phase 3
0.7485	Intermediate Similarity	NPD37	Approved
0.7485	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD7228	Approved
0.7472	Intermediate Similarity	NPD3818	Discontinued
0.7457	Intermediate Similarity	NPD4967	Phase 2
0.7457	Intermediate Similarity	NPD4966	Approved
0.7457	Intermediate Similarity	NPD4965	Approved
0.7442	Intermediate Similarity	NPD8455	Phase 2
0.7442	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1512	Approved
0.7432	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7054	Approved
0.7429	Intermediate Similarity	NPD5494	Approved
0.7421	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD8313	Approved
0.7418	Intermediate Similarity	NPD8312	Approved
0.7416	Intermediate Similarity	NPD7473	Discontinued
0.7403	Intermediate Similarity	NPD1610	Phase 2
0.7399	Intermediate Similarity	NPD3817	Phase 2
0.7389	Intermediate Similarity	NPD7472	Approved
0.7384	Intermediate Similarity	NPD6801	Discontinued
0.7378	Intermediate Similarity	NPD5763	Approved
0.7378	Intermediate Similarity	NPD5762	Approved
0.7371	Intermediate Similarity	NPD6234	Discontinued
0.7368	Intermediate Similarity	NPD6599	Discontinued
0.7362	Intermediate Similarity	NPD1510	Phase 2
0.7356	Intermediate Similarity	NPD7768	Phase 2
0.7345	Intermediate Similarity	NPD6232	Discontinued
0.7341	Intermediate Similarity	NPD2801	Approved
0.7341	Intermediate Similarity	NPD5761	Phase 2
0.7341	Intermediate Similarity	NPD1465	Phase 2
0.7341	Intermediate Similarity	NPD5760	Phase 2
0.7329	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1613	Approved
0.7329	Intermediate Similarity	NPD4140	Approved
0.7321	Intermediate Similarity	NPD1511	Approved
0.7321	Intermediate Similarity	NPD7390	Discontinued
0.7317	Intermediate Similarity	NPD2796	Approved
0.731	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD5403	Approved
0.7288	Intermediate Similarity	NPD8127	Discontinued
0.7284	Intermediate Similarity	NPD6355	Discontinued
0.7256	Intermediate Similarity	NPD3748	Approved
0.7246	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6799	Approved
0.7213	Intermediate Similarity	NPD6559	Discontinued
0.7205	Intermediate Similarity	NPD6798	Discontinued
0.7205	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD2800	Approved
0.7178	Intermediate Similarity	NPD5735	Approved
0.7176	Intermediate Similarity	NPD2534	Approved
0.7176	Intermediate Similarity	NPD2533	Approved
0.7176	Intermediate Similarity	NPD5401	Approved
0.7176	Intermediate Similarity	NPD2532	Approved
0.7169	Intermediate Similarity	NPD6002	Phase 3
0.7169	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6005	Phase 3
0.7169	Intermediate Similarity	NPD6004	Phase 3
0.7169	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD3892	Phase 2
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7143	Intermediate Similarity	NPD4628	Phase 3
0.7126	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7685	Pre-registration
0.712	Intermediate Similarity	NPD7240	Approved
0.7117	Intermediate Similarity	NPD1240	Approved
0.7117	Intermediate Similarity	NPD4060	Phase 1
0.7101	Intermediate Similarity	NPD6190	Approved
0.7089	Intermediate Similarity	NPD5327	Phase 3
0.7081	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6780	Approved
0.7062	Intermediate Similarity	NPD6779	Approved
0.7062	Intermediate Similarity	NPD6778	Approved
0.7062	Intermediate Similarity	NPD6782	Approved
0.7062	Intermediate Similarity	NPD6781	Approved
0.7062	Intermediate Similarity	NPD6776	Approved
0.7062	Intermediate Similarity	NPD6777	Approved
0.7059	Intermediate Similarity	NPD7236	Approved
0.7055	Intermediate Similarity	NPD6663	Approved
0.7055	Intermediate Similarity	NPD8032	Phase 2
0.7055	Intermediate Similarity	NPD6233	Phase 2
0.7041	Intermediate Similarity	NPD4002	Approved
0.7041	Intermediate Similarity	NPD7003	Approved
0.7041	Intermediate Similarity	NPD4004	Approved
0.7041	Intermediate Similarity	NPD7435	Discontinued
0.7032	Intermediate Similarity	NPD1548	Phase 1
0.703	Intermediate Similarity	NPD6353	Approved
0.703	Intermediate Similarity	NPD1607	Approved
0.7026	Intermediate Similarity	NPD3452	Approved
0.7026	Intermediate Similarity	NPD3450	Approved
0.7026	Intermediate Similarity	NPD2494	Approved
0.7026	Intermediate Similarity	NPD2493	Approved
0.7025	Intermediate Similarity	NPD1608	Approved
0.7021	Intermediate Similarity	NPD8434	Phase 2
0.7019	Intermediate Similarity	NPD5736	Approved
0.7019	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD3926	Phase 2
0.7011	Intermediate Similarity	NPD3226	Approved
0.7005	Intermediate Similarity	NPD4583	Approved
0.7005	Intermediate Similarity	NPD7870	Phase 2
0.7005	Intermediate Similarity	NPD7871	Phase 2
0.7005	Intermediate Similarity	NPD4582	Approved
0.6995	Remote Similarity	NPD2973	Approved
0.6995	Remote Similarity	NPD2974	Approved
0.6995	Remote Similarity	NPD2975	Approved
0.6981	Remote Similarity	NPD4749	Approved
0.6974	Remote Similarity	NPD4580	Approved
0.6954	Remote Similarity	NPD7696	Phase 3
0.6954	Remote Similarity	NPD7698	Approved
0.6954	Remote Similarity	NPD7697	Approved
0.6954	Remote Similarity	NPD7239	Suspended
0.6947	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3019	Approved
0.6935	Remote Similarity	NPD6765	Approved
0.6935	Remote Similarity	NPD6764	Approved
0.6933	Remote Similarity	NPD7095	Approved
0.6933	Remote Similarity	NPD3027	Phase 3
0.6931	Remote Similarity	NPD8150	Discontinued
0.6919	Remote Similarity	NPD7212	Phase 2
0.6919	Remote Similarity	NPD7213	Phase 3
0.6914	Remote Similarity	NPD7458	Discontinued
0.6911	Remote Similarity	NPD2488	Approved
0.6911	Remote Similarity	NPD2490	Approved
0.6909	Remote Similarity	NPD3620	Phase 2
0.6909	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3094	Phase 2
0.689	Remote Similarity	NPD3268	Approved
0.689	Remote Similarity	NPD3764	Approved
0.6886	Remote Similarity	NPD7097	Phase 1
0.6882	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7447	Phase 1
0.6867	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5124	Phase 1
0.6866	Remote Similarity	NPD8151	Discontinued
0.6864	Remote Similarity	NPD2344	Approved
0.6859	Remote Similarity	NPD4287	Approved
0.6852	Remote Similarity	NPD4624	Approved
0.6852	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD17	Approved
0.6835	Remote Similarity	NPD2932	Approved
0.6832	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7874	Approved
0.6826	Remote Similarity	NPD6653	Approved
0.6826	Remote Similarity	NPD6651	Approved
0.6821	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7701	Phase 2
0.6815	Remote Similarity	NPD3091	Approved
0.6813	Remote Similarity	NPD1247	Approved
0.6811	Remote Similarity	NPD7177	Discontinued
0.6805	Remote Similarity	NPD1551	Phase 2

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