NPASS Compound

Structure

NPC95899 OpenBabel07101718202D 31 34 0 0 1 0 0 0 0 0999 V2000 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -3.8660 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 0.5000 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 0.0000 2.0000 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 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 3 24 1 0 0 0 0 4 24 1 0 0 0 0 8 10 1 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 9 20 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 19 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 14 23 1 0 0 0 0 15 18 2 0 0 0 0 15 27 1 0 0 0 0 16 18 1 0 0 0 0 16 28 2 0 0 0 0 17 29 2 0 0 0 0 17 31 1 0 0 0 0 18 19 1 0 0 0 0 19 30 1 6 0 0 0 20 24 1 0 0 0 0 20 25 1 6 0 0 0 21 26 1 6 0 0 0 21 27 1 0 0 0 0 22 25 1 6 0 0 0 22 26 1 0 0 0 0 23 27 1 1 0 0 0 23 31 1 0 0 0 0 25 5 1 6 0 0 0 26 6 1 6 0 0 0 27 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.31
Volume:	468.574
LogP:	4.317
LogD:	3.912
LogS:	-4.315
# Rotatable Bonds:	3
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.59
Synthetic Accessibility Score:	4.856
Fsp3:	0.852
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.728
MDCK Permeability:	2.0835219402215444e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.961
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.556
Plasma Protein Binding (PPB):	86.45335388183594%
Volume Distribution (VD):	0.935
Pgp-substrate:	18.015892028808594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.125
CYP2C19-inhibitor:	0.045
CYP2C19-substrate:	0.741
CYP2C9-inhibitor:	0.234
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.652
CYP3A4-substrate:	0.436

ADMET: Excretion

Clearance (CL):	4.696
Half-life (T1/2):	0.127

ADMET: Toxicity

hERG Blockers:	0.231
Human Hepatotoxicity (H-HT):	0.577
Drug-inuced Liver Injury (DILI):	0.106
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.956
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.942
Carcinogencity:	0.687
Eye Corrosion:	0.791
Eye Irritation:	0.314
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC95899

Natural Product ID:	NPC95899
*Common Name:**	Flabelliferin B
IUPAC Name:	[(4aS,4bR,6S,6aR,9S,10aS,10bR,12aS)-8-acetyl-9-hydroxy-1,1,4a,6a,10b-pentamethyl-2,3,4,4b,5,6,9,10,10a,11,12,12a-dodecahydrochrysen-6-yl] acetate
Synonyms:	Flabelliferin B
Standard InCHIKey:	JBPWKIMADBDSID-QGERINELSA-N
Standard InCHI:	InChI=1S/C27H42O4/c1-16(28)18-15-27(7)21(13-19(18)30)26(6)12-9-20-24(3,4)10-8-11-25(20,5)22(26)14-23(27)31-17(2)29/h15,19-23,30H,8-14H2,1-7H3/t19-,20-,21-,22+,23-,25-,26-,27+/m0/s1
SMILES:	CC(=O)O[C@H]1C[C@H]2[C@@]([C@H]3[C@@]1(C)C=C(C(=O)C)[C@H](C3)O)(C)CC[C@@H]1[C@]2(C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2087231
PubChem CID:	66554038
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001093] Carboxylic acid derivatives [CHEMONTID:0001238] Carboxylic acid esters

*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
NPO6368	Carteriospongia flabellifera	Species	Thorectidae	Eukaryota	n.a.	South Pacific	n.a.	PMID[22834941]
NPO6368	Carteriospongia flabellifera	Species	Thorectidae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT386	Cell Line	KM12	Homo sapiens	IC50	<	10000.0	nM	PMID[505140]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	<	10000.0	nM	PMID[505140]
NPT386	Cell Line	KM12	Homo sapiens	IC50	=	18000.0	nM	PMID[505140]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	20000.0	nM	PMID[505140]

☑ 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 NPC95899 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	224
0.1-0.2	1268
0.2-0.3	3815
0.3-0.4	7211
0.4-0.5	13135
0.5-0.6	7493
0.6-0.7	5318
0.7-0.8	3730
0.8-0.85	449
0.85-0.9	45
0.9-0.95	1
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9388	High Similarity	NPC478057
0.9175	High Similarity	NPC478056
0.8857	High Similarity	NPC277769
0.8857	High Similarity	NPC90952
0.8835	High Similarity	NPC275539
0.8835	High Similarity	NPC189075
0.8812	High Similarity	NPC95585
0.8812	High Similarity	NPC90177
0.8812	High Similarity	NPC476889
0.8812	High Similarity	NPC282233
0.8776	High Similarity	NPC98874
0.8738	High Similarity	NPC110496
0.8713	High Similarity	NPC476890
0.8713	High Similarity	NPC40918
0.87	High Similarity	NPC471041
0.8687	High Similarity	NPC26413
0.8687	High Similarity	NPC89225
0.8679	High Similarity	NPC4573
0.8673	High Similarity	NPC148523
0.8673	High Similarity	NPC474727
0.866	High Similarity	NPC214756
0.866	High Similarity	NPC272075
0.866	High Similarity	NPC295643
0.8654	High Similarity	NPC473483
0.8646	High Similarity	NPC232202
0.8614	High Similarity	NPC476888
0.8614	High Similarity	NPC93744
0.86	High Similarity	NPC316598
0.8598	High Similarity	NPC472926
0.8586	High Similarity	NPC167193
0.8586	High Similarity	NPC472806
0.8586	High Similarity	NPC202833
0.8571	High Similarity	NPC47853
0.8571	High Similarity	NPC31522
0.8571	High Similarity	NPC74751
0.8558	High Similarity	NPC475570
0.8558	High Similarity	NPC472925
0.8557	High Similarity	NPC145067
0.8557	High Similarity	NPC4036
0.8557	High Similarity	NPC233455
0.8557	High Similarity	NPC158030
0.8557	High Similarity	NPC65120
0.8532	High Similarity	NPC134430
0.8529	High Similarity	NPC165250
0.8529	High Similarity	NPC136289
0.8515	High Similarity	NPC251680
0.8515	High Similarity	NPC476299
0.8515	High Similarity	NPC474012
0.8515	High Similarity	NPC306856
0.8515	High Similarity	NPC117685
0.8505	High Similarity	NPC194951
0.8505	High Similarity	NPC12046
0.85	High Similarity	NPC476879
0.85	High Similarity	NPC320306
0.85	High Similarity	NPC253826
0.85	High Similarity	NPC476878
0.85	High Similarity	NPC189880
0.85	High Similarity	NPC108078
0.85	High Similarity	NPC170131
0.8485	Intermediate Similarity	NPC195715
0.8476	Intermediate Similarity	NPC476802
0.8476	Intermediate Similarity	NPC89171
0.8476	Intermediate Similarity	NPC90946
0.8476	Intermediate Similarity	NPC300614
0.8462	Intermediate Similarity	NPC80566
0.8454	Intermediate Similarity	NPC474728
0.8447	Intermediate Similarity	NPC471208
0.8447	Intermediate Similarity	NPC254202
0.8447	Intermediate Similarity	NPC275583
0.8447	Intermediate Similarity	NPC131366
0.8438	Intermediate Similarity	NPC104560
0.8431	Intermediate Similarity	NPC471412
0.8431	Intermediate Similarity	NPC97435
0.8431	Intermediate Similarity	NPC472924
0.8431	Intermediate Similarity	NPC81530
0.8426	Intermediate Similarity	NPC157441
0.8426	Intermediate Similarity	NPC122056
0.8426	Intermediate Similarity	NPC25909
0.8421	Intermediate Similarity	NPC322159
0.8421	Intermediate Similarity	NPC472986
0.8421	Intermediate Similarity	NPC472985
0.8416	Intermediate Similarity	NPC78427
0.8416	Intermediate Similarity	NPC260149
0.8416	Intermediate Similarity	NPC58942
0.8416	Intermediate Similarity	NPC475876
0.8416	Intermediate Similarity	NPC16911
0.8416	Intermediate Similarity	NPC174663
0.8416	Intermediate Similarity	NPC471966
0.8411	Intermediate Similarity	NPC474315
0.84	Intermediate Similarity	NPC7124
0.84	Intermediate Similarity	NPC329910
0.84	Intermediate Similarity	NPC134072
0.84	Intermediate Similarity	NPC234993
0.84	Intermediate Similarity	NPC242848
0.8393	Intermediate Similarity	NPC67569
0.8384	Intermediate Similarity	NPC209868
0.8384	Intermediate Similarity	NPC474529
0.8384	Intermediate Similarity	NPC78580
0.8384	Intermediate Similarity	NPC23621
0.8384	Intermediate Similarity	NPC469982
0.8384	Intermediate Similarity	NPC184006
0.8384	Intermediate Similarity	NPC159365
0.8384	Intermediate Similarity	NPC91010
0.8384	Intermediate Similarity	NPC119562
0.8384	Intermediate Similarity	NPC279410
0.8378	Intermediate Similarity	NPC473636
0.8378	Intermediate Similarity	NPC77689
0.8367	Intermediate Similarity	NPC155120
0.8367	Intermediate Similarity	NPC324341
0.8367	Intermediate Similarity	NPC282616
0.8367	Intermediate Similarity	NPC966
0.8367	Intermediate Similarity	NPC470590
0.8367	Intermediate Similarity	NPC6255
0.8367	Intermediate Similarity	NPC471588
0.8367	Intermediate Similarity	NPC73457
0.8367	Intermediate Similarity	NPC288833
0.8367	Intermediate Similarity	NPC60755
0.8367	Intermediate Similarity	NPC285184
0.8367	Intermediate Similarity	NPC228784
0.8367	Intermediate Similarity	NPC77099
0.8367	Intermediate Similarity	NPC198054
0.8365	Intermediate Similarity	NPC475036
0.8365	Intermediate Similarity	NPC222161
0.8365	Intermediate Similarity	NPC96268
0.8364	Intermediate Similarity	NPC472927
0.8364	Intermediate Similarity	NPC475809
0.8351	Intermediate Similarity	NPC314727
0.8351	Intermediate Similarity	NPC198664
0.8351	Intermediate Similarity	NPC477973
0.8351	Intermediate Similarity	NPC470588
0.8351	Intermediate Similarity	NPC281524
0.8351	Intermediate Similarity	NPC143232
0.8351	Intermediate Similarity	NPC474700
0.8351	Intermediate Similarity	NPC274330
0.835	Intermediate Similarity	NPC293753
0.835	Intermediate Similarity	NPC137430
0.8349	Intermediate Similarity	NPC147912
0.8349	Intermediate Similarity	NPC67259
0.8333	Intermediate Similarity	NPC472972
0.8333	Intermediate Similarity	NPC266955
0.8333	Intermediate Similarity	NPC287676
0.8333	Intermediate Similarity	NPC327431
0.8333	Intermediate Similarity	NPC475156
0.8333	Intermediate Similarity	NPC471413
0.8333	Intermediate Similarity	NPC476767
0.8333	Intermediate Similarity	NPC473576
0.8333	Intermediate Similarity	NPC269530
0.8319	Intermediate Similarity	NPC23786
0.8319	Intermediate Similarity	NPC470265
0.8318	Intermediate Similarity	NPC197428
0.8318	Intermediate Similarity	NPC179642
0.8317	Intermediate Similarity	NPC473456
0.8317	Intermediate Similarity	NPC287668
0.8317	Intermediate Similarity	NPC224356
0.8317	Intermediate Similarity	NPC132753
0.8317	Intermediate Similarity	NPC121402
0.8317	Intermediate Similarity	NPC151681
0.8317	Intermediate Similarity	NPC175351
0.8304	Intermediate Similarity	NPC476962
0.8302	Intermediate Similarity	NPC322903
0.8302	Intermediate Similarity	NPC476765
0.8302	Intermediate Similarity	NPC151393
0.8302	Intermediate Similarity	NPC325054
0.83	Intermediate Similarity	NPC470232
0.83	Intermediate Similarity	NPC473240
0.83	Intermediate Similarity	NPC23241
0.83	Intermediate Similarity	NPC139570
0.83	Intermediate Similarity	NPC470229
0.8288	Intermediate Similarity	NPC251310
0.8288	Intermediate Similarity	NPC21326
0.8286	Intermediate Similarity	NPC231530
0.8286	Intermediate Similarity	NPC111952
0.8286	Intermediate Similarity	NPC278628
0.8283	Intermediate Similarity	NPC86368
0.8283	Intermediate Similarity	NPC298554
0.8283	Intermediate Similarity	NPC151722
0.8283	Intermediate Similarity	NPC199543
0.8273	Intermediate Similarity	NPC268954
0.8273	Intermediate Similarity	NPC44170
0.8269	Intermediate Similarity	NPC159442
0.8269	Intermediate Similarity	NPC72151
0.8269	Intermediate Similarity	NPC99266
0.8269	Intermediate Similarity	NPC8196
0.8265	Intermediate Similarity	NPC120840
0.8265	Intermediate Similarity	NPC86372
0.8265	Intermediate Similarity	NPC470589
0.8265	Intermediate Similarity	NPC126369
0.8265	Intermediate Similarity	NPC172361
0.8265	Intermediate Similarity	NPC111110
0.8265	Intermediate Similarity	NPC291028
0.8265	Intermediate Similarity	NPC113989
0.8257	Intermediate Similarity	NPC159333
0.8252	Intermediate Similarity	NPC163963
0.8252	Intermediate Similarity	NPC52899
0.8252	Intermediate Similarity	NPC282524
0.8252	Intermediate Similarity	NPC115862
0.8252	Intermediate Similarity	NPC115899
0.8252	Intermediate Similarity	NPC289148
0.8247	Intermediate Similarity	NPC48107
0.8247	Intermediate Similarity	NPC474512

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 NPC95899 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	1523
0.2-0.3	3420
0.3-0.4	2502
0.4-0.5	949
0.5-0.6	275
0.6-0.7	187
0.7-0.8	92
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
0.8571	High Similarity	NPD7748	Approved
0.8557	High Similarity	NPD7515	Phase 2
0.8515	High Similarity	NPD7639	Approved
0.8515	High Similarity	NPD7640	Approved
0.8416	Intermediate Similarity	NPD7638	Approved
0.8317	Intermediate Similarity	NPD7902	Approved
0.8198	Intermediate Similarity	NPD7115	Discovery
0.802	Intermediate Similarity	NPD7900	Approved
0.802	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD4225	Approved
0.783	Intermediate Similarity	NPD7632	Discontinued
0.7745	Intermediate Similarity	NPD5779	Approved
0.7745	Intermediate Similarity	NPD5778	Approved
0.7745	Intermediate Similarity	NPD6399	Phase 3
0.77	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD3618	Phase 1
0.7647	Intermediate Similarity	NPD6079	Approved
0.7636	Intermediate Similarity	NPD6881	Approved
0.7636	Intermediate Similarity	NPD6899	Approved
0.7627	Intermediate Similarity	NPD8328	Phase 3
0.7624	Intermediate Similarity	NPD5328	Approved
0.7615	Intermediate Similarity	NPD6675	Approved
0.7615	Intermediate Similarity	NPD6402	Approved
0.7615	Intermediate Similarity	NPD7128	Approved
0.7615	Intermediate Similarity	NPD5739	Approved
0.76	Intermediate Similarity	NPD3573	Approved
0.7545	Intermediate Similarity	NPD5697	Approved
0.7521	Intermediate Similarity	NPD6319	Approved
0.7521	Intermediate Similarity	NPD7736	Approved
0.75	Intermediate Similarity	NPD6684	Approved
0.75	Intermediate Similarity	NPD7290	Approved
0.75	Intermediate Similarity	NPD7334	Approved
0.75	Intermediate Similarity	NPD7146	Approved
0.75	Intermediate Similarity	NPD7521	Approved
0.75	Intermediate Similarity	NPD6409	Approved
0.75	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD7102	Approved
0.75	Intermediate Similarity	NPD5330	Approved
0.7477	Intermediate Similarity	NPD6011	Approved
0.7477	Intermediate Similarity	NPD7320	Approved
0.7477	Intermediate Similarity	NPD6686	Approved
0.7476	Intermediate Similarity	NPD6411	Approved
0.7475	Intermediate Similarity	NPD4786	Approved
0.7456	Intermediate Similarity	NPD4632	Approved
0.7455	Intermediate Similarity	NPD6008	Approved
0.7453	Intermediate Similarity	NPD6083	Phase 2
0.7453	Intermediate Similarity	NPD6084	Phase 2
0.7451	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD3667	Approved
0.7434	Intermediate Similarity	NPD6617	Approved
0.7434	Intermediate Similarity	NPD6869	Approved
0.7434	Intermediate Similarity	NPD6649	Approved
0.7434	Intermediate Similarity	NPD6847	Approved
0.7434	Intermediate Similarity	NPD8130	Phase 1
0.7434	Intermediate Similarity	NPD6650	Approved
0.7417	Intermediate Similarity	NPD7492	Approved
0.7411	Intermediate Similarity	NPD6373	Approved
0.7411	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD6372	Approved
0.7411	Intermediate Similarity	NPD6014	Approved
0.7411	Intermediate Similarity	NPD6013	Approved
0.7411	Intermediate Similarity	NPD6012	Approved
0.74	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD6412	Phase 2
0.7387	Intermediate Similarity	NPD5701	Approved
0.7373	Intermediate Similarity	NPD6054	Approved
0.7368	Intermediate Similarity	NPD6882	Approved
0.7368	Intermediate Similarity	NPD8297	Approved
0.7358	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5222	Approved
0.7358	Intermediate Similarity	NPD5221	Approved
0.7355	Intermediate Similarity	NPD6616	Approved
0.7353	Intermediate Similarity	NPD6903	Approved
0.7353	Intermediate Similarity	NPD6672	Approved
0.7353	Intermediate Similarity	NPD5737	Approved
0.7339	Intermediate Similarity	NPD5211	Phase 2
0.7327	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7319	Approved
0.7308	Intermediate Similarity	NPD8034	Phase 2
0.7308	Intermediate Similarity	NPD8035	Phase 2
0.7308	Intermediate Similarity	NPD7637	Suspended
0.73	Intermediate Similarity	NPD3665	Phase 1
0.73	Intermediate Similarity	NPD3133	Approved
0.73	Intermediate Similarity	NPD3666	Approved
0.7295	Intermediate Similarity	NPD7078	Approved
0.729	Intermediate Similarity	NPD5173	Approved
0.7282	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6101	Approved
0.7281	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD6009	Approved
0.7257	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6370	Approved
0.7245	Intermediate Similarity	NPD4695	Discontinued
0.7238	Intermediate Similarity	NPD4202	Approved
0.7228	Intermediate Similarity	NPD1694	Approved
0.7227	Intermediate Similarity	NPD6059	Approved
0.7213	Intermediate Similarity	NPD7507	Approved
0.7212	Intermediate Similarity	NPD5785	Approved
0.7207	Intermediate Similarity	NPD5141	Approved
0.7196	Intermediate Similarity	NPD4697	Phase 3
0.7193	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4634	Approved
0.719	Intermediate Similarity	NPD7604	Phase 2
0.7179	Intermediate Similarity	NPD6868	Approved
0.7168	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD5983	Phase 2
0.7167	Intermediate Similarity	NPD6015	Approved
0.7167	Intermediate Similarity	NPD6016	Approved
0.7156	Intermediate Similarity	NPD5285	Approved
0.7156	Intermediate Similarity	NPD5286	Approved
0.7156	Intermediate Similarity	NPD4696	Approved
0.7154	Intermediate Similarity	NPD8293	Discontinued
0.7143	Intermediate Similarity	NPD7645	Phase 2
0.713	Intermediate Similarity	NPD4755	Approved
0.7107	Intermediate Similarity	NPD5988	Approved
0.7103	Intermediate Similarity	NPD5695	Phase 3
0.7103	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5223	Approved
0.7073	Intermediate Similarity	NPD6336	Discontinued
0.7064	Intermediate Similarity	NPD5696	Approved
0.7059	Intermediate Similarity	NPD5363	Approved
0.7059	Intermediate Similarity	NPD6335	Approved
0.7043	Intermediate Similarity	NPD6371	Approved
0.7037	Intermediate Similarity	NPD7614	Phase 1
0.7034	Intermediate Similarity	NPD6274	Approved
0.7027	Intermediate Similarity	NPD5225	Approved
0.7027	Intermediate Similarity	NPD5224	Approved
0.7027	Intermediate Similarity	NPD4633	Approved
0.7027	Intermediate Similarity	NPD5226	Approved
0.7	Intermediate Similarity	NPD4700	Approved
0.7	Intermediate Similarity	NPD7100	Approved
0.7	Intermediate Similarity	NPD7101	Approved
0.699	Remote Similarity	NPD4519	Discontinued
0.699	Remote Similarity	NPD4623	Approved
0.6975	Remote Similarity	NPD6317	Approved
0.6964	Remote Similarity	NPD5175	Approved
0.6964	Remote Similarity	NPD5174	Approved
0.6961	Remote Similarity	NPD3668	Phase 3
0.6952	Remote Similarity	NPD4753	Phase 2
0.6952	Remote Similarity	NPD6904	Approved
0.6952	Remote Similarity	NPD6673	Approved
0.6952	Remote Similarity	NPD6080	Approved
0.6937	Remote Similarity	NPD5344	Discontinued
0.693	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6053	Discontinued
0.6917	Remote Similarity	NPD7328	Approved
0.6917	Remote Similarity	NPD7327	Approved
0.6917	Remote Similarity	NPD6313	Approved
0.6917	Remote Similarity	NPD6314	Approved
0.6887	Remote Similarity	NPD46	Approved
0.6887	Remote Similarity	NPD6698	Approved
0.6885	Remote Similarity	NPD8033	Approved
0.6881	Remote Similarity	NPD7732	Phase 3
0.6869	Remote Similarity	NPD6115	Approved
0.6869	Remote Similarity	NPD6697	Approved
0.6869	Remote Similarity	NPD6118	Approved
0.6869	Remote Similarity	NPD6114	Approved
0.686	Remote Similarity	NPD7516	Approved
0.6827	Remote Similarity	NPD5279	Phase 3
0.6825	Remote Similarity	NPD6033	Approved
0.6822	Remote Similarity	NPD5693	Phase 1
0.6822	Remote Similarity	NPD7983	Approved
0.6814	Remote Similarity	NPD4754	Approved
0.6803	Remote Similarity	NPD8377	Approved
0.6803	Remote Similarity	NPD8294	Approved
0.6789	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4629	Approved
0.6789	Remote Similarity	NPD5210	Approved
0.6774	Remote Similarity	NPD6067	Discontinued
0.6765	Remote Similarity	NPD4221	Approved
0.6765	Remote Similarity	NPD4270	Approved
0.6765	Remote Similarity	NPD4223	Phase 3
0.6765	Remote Similarity	NPD4269	Approved
0.6748	Remote Similarity	NPD8515	Approved
0.6748	Remote Similarity	NPD8380	Approved
0.6748	Remote Similarity	NPD8335	Approved
0.6748	Remote Similarity	NPD8513	Phase 3
0.6748	Remote Similarity	NPD6908	Approved
0.6748	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD8379	Approved
0.6748	Remote Similarity	NPD8296	Approved
0.6748	Remote Similarity	NPD8517	Approved
0.6748	Remote Similarity	NPD7503	Approved
0.6748	Remote Similarity	NPD8516	Approved
0.6748	Remote Similarity	NPD6909	Approved
0.6748	Remote Similarity	NPD8378	Approved
0.6733	Remote Similarity	NPD7525	Registered
0.6731	Remote Similarity	NPD5329	Approved
0.6724	Remote Similarity	NPD4730	Approved
0.6724	Remote Similarity	NPD5168	Approved
0.6724	Remote Similarity	NPD4729	Approved
0.6724	Remote Similarity	NPD5128	Approved
0.6723	Remote Similarity	NPD8133	Approved
0.67	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4788	Approved
0.6698	Remote Similarity	NPD5208	Approved
0.6697	Remote Similarity	NPD5282	Discontinued
0.6697	Remote Similarity	NPD6001	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