NPASS Compound

Structure

NPC470438 OpenBabel07101719132D 50 54 0 0 1 0 0 0 0 0999 V2000 -5.1017 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2514 4.4182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2514 0.4909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1017 -0.9818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2514 3.4364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4011 4.9091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4011 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2514 -1.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4011 2.9455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5508 4.4182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4011 1.9636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5508 1.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2514 0.4909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3495 -3.1996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4011 -0.9818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7006 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4011 -0.9818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5508 3.4364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4011 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2514 1.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6036 -4.1479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5508 0.4909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8503 0.4909 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9093 -4.8422 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8503 1.4727 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.9636 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9610 -4.5881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8503 1.4727 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7069 -3.6397 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5508 -1.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7006 2.9455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8503 0.4909 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5508 -2.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4011 -2.9455 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.1017 1.9636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5520 -4.4020 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1635 -5.7905 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7006 1.9636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9455 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2667 -5.2823 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8101 -3.1315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5508 -2.4545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8503 3.4364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7006 -2.9455 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1800 -2.3478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7006 -0.9818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5508 -1.4727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7006 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7006 1.9636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 17 2 0 0 0 0 8 17 1 0 0 0 0 9 18 2 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 20 2 0 0 0 0 12 22 2 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 14 34 1 0 0 0 0 15 19 1 0 0 0 0 15 47 1 0 0 0 0 16 46 1 0 0 0 0 17 30 1 0 0 0 0 18 31 1 0 0 0 0 19 22 1 0 0 0 0 20 35 1 0 0 0 0 21 24 1 0 0 0 0 21 36 2 0 0 0 0 22 48 1 0 0 0 0 23 16 1 6 0 0 0 23 25 1 0 0 0 0 23 49 1 0 0 0 0 24 27 1 0 0 0 0 24 37 1 1 0 0 0 25 26 1 0 0 0 0 25 38 1 1 0 0 0 26 28 1 0 0 0 0 26 39 1 6 0 0 0 27 29 1 0 0 0 0 27 40 1 1 0 0 0 28 32 1 0 0 0 0 28 50 1 1 0 0 0 29 34 1 1 0 0 0 29 41 1 0 0 0 0 30 42 2 0 0 0 0 30 46 1 0 0 0 0 31 43 2 0 0 0 0 31 50 1 0 0 0 0 32 48 1 6 0 0 0 32 49 1 0 0 0 0 33 34 1 0 0 0 0 33 44 2 0 0 0 0 33 47 1 0 0 0 0 34 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	698.18
Volume:	660.207
LogP:	1.736
LogD:	1.094
LogS:	-2.742
# Rotatable Bonds:	13
TPSA:	256.04
# H-Bond Aceptor:	16
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.1
Synthetic Accessibility Score:	4.767
Fsp3:	0.353
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.548
MDCK Permeability:	3.084124546148814e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.624
Human Intestinal Absorption (HIA):	0.901
20% Bioavailability (F20%):	0.923
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.14
Plasma Protein Binding (PPB):	98.31703186035156%
Volume Distribution (VD):	0.518
Pgp-substrate:	4.329304218292236%

ADMET: Metabolism

CYP1A2-inhibitor:	0.061
CYP1A2-substrate:	0.025
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.187
CYP2D6-inhibitor:	0.367
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.053

ADMET: Excretion

Clearance (CL):	4.402
Half-life (T1/2):	0.9

ADMET: Toxicity

hERG Blockers:	0.219
Human Hepatotoxicity (H-HT):	0.098
Drug-inuced Liver Injury (DILI):	0.941
AMES Toxicity:	0.07
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.0
Skin Sensitization:	0.016
Carcinogencity:	0.087
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.001

Download Data

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

Natural Product: NPC470438

Natural Product ID:	NPC470438
*Common Name:**	Flacourtoside D
IUPAC Name:	[2-[(2S,3R,4S,5S,6R)-3-benzoyloxy-6-(benzoyloxymethyl)-4,5-dihydroxyoxan-2-yl]oxy-5-hydroxyphenyl]methyl (2R,3S,4S)-1,2,3,4-tetrahydroxy-5-oxocyclohexane-1-carboxylate
Synonyms:	Flacourtoside D
Standard InCHIKey:	FRYKICRRHMPZIS-VCGSQPFVSA-N
Standard InCHI:	InChI=1S/C34H34O16/c35-20-11-12-22(19(13-20)15-47-33(44)34(45)14-21(36)24(37)27(40)29(34)41)48-32-28(50-31(43)18-9-5-2-6-10-18)26(39)25(38)23(49-32)16-46-30(42)17-7-3-1-4-8-17/h1-13,23-29,32,35,37-41,45H,14-16H2/t23-,24-,25-,26+,27-,28-,29-,32-,34?/m1/s1
SMILES:	C1C(=O)C(C(C(C1(C(=O)OCC2=C(C=CC(=C2)O)OC3C(C(C(C(O3)COC(=O)C4=CC=CC=C4)O)O)OC(=O)C5=CC=CC=C5)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2036486
PubChem CID:	57409246
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO33462	flacourtia ramontchi	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22439591]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	35500.0	nM	PMID[484293]

☑ 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 NPC470438 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	415
0.1-0.2	1739
0.2-0.3	3935
0.3-0.4	8428
0.4-0.5	9173
0.5-0.6	5573
0.6-0.7	6346
0.7-0.8	5732
0.8-0.85	907
0.85-0.9	435
0.9-0.95	13
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9512	High Similarity	NPC280385
0.9506	High Similarity	NPC280923
0.9329	High Similarity	NPC475174
0.9325	High Similarity	NPC475183
0.9198	High Similarity	NPC57072
0.9198	High Similarity	NPC231475
0.907	High Similarity	NPC97119
0.907	High Similarity	NPC297503
0.907	High Similarity	NPC135831
0.9042	High Similarity	NPC128403
0.9018	High Similarity	NPC474398
0.9018	High Similarity	NPC474441
0.9018	High Similarity	NPC474401
0.9018	High Similarity	NPC476026
0.9017	High Similarity	NPC470416
0.9006	High Similarity	NPC113836
0.9006	High Similarity	NPC37668
0.9006	High Similarity	NPC253521
0.8988	High Similarity	NPC95421
0.8988	High Similarity	NPC198125
0.8976	High Similarity	NPC227297
0.897	High Similarity	NPC132737
0.8966	High Similarity	NPC474093
0.8966	High Similarity	NPC104910
0.896	High Similarity	NPC156785
0.896	High Similarity	NPC162394
0.896	High Similarity	NPC36138
0.896	High Similarity	NPC241781
0.896	High Similarity	NPC470718
0.8951	High Similarity	NPC92153
0.8951	High Similarity	NPC230439
0.8951	High Similarity	NPC279281
0.8951	High Similarity	NPC299761
0.8947	High Similarity	NPC472991
0.8947	High Similarity	NPC472992
0.8947	High Similarity	NPC61904
0.8947	High Similarity	NPC144097
0.8935	High Similarity	NPC469344
0.8935	High Similarity	NPC96605
0.8935	High Similarity	NPC188815
0.8935	High Similarity	NPC470712
0.8935	High Similarity	NPC164704
0.8935	High Similarity	NPC218161
0.8935	High Similarity	NPC280642
0.8914	High Similarity	NPC30011
0.8914	High Similarity	NPC97817
0.8914	High Similarity	NPC475179
0.8914	High Similarity	NPC72554
0.8908	High Similarity	NPC470717
0.8908	High Similarity	NPC460984
0.8908	High Similarity	NPC470713
0.8908	High Similarity	NPC25946
0.8908	High Similarity	NPC470720
0.8908	High Similarity	NPC223860
0.8908	High Similarity	NPC470451
0.8908	High Similarity	NPC249560
0.8908	High Similarity	NPC275977
0.8908	High Similarity	NPC470455
0.8908	High Similarity	NPC21359
0.8902	High Similarity	NPC469371
0.8895	High Similarity	NPC293626
0.8895	High Similarity	NPC217387
0.8895	High Similarity	NPC476621
0.8895	High Similarity	NPC472387
0.8895	High Similarity	NPC476619
0.8895	High Similarity	NPC477895
0.8895	High Similarity	NPC476622
0.8895	High Similarity	NPC476618
0.8895	High Similarity	NPC267680
0.8895	High Similarity	NPC35167
0.8895	High Similarity	NPC258044
0.8895	High Similarity	NPC196127
0.8895	High Similarity	NPC476620
0.8895	High Similarity	NPC476623
0.8889	High Similarity	NPC214621
0.8889	High Similarity	NPC223426
0.8889	High Similarity	NPC34267
0.8889	High Similarity	NPC81042
0.8882	High Similarity	NPC217822
0.8882	High Similarity	NPC5786
0.8882	High Similarity	NPC102851
0.8882	High Similarity	NPC470714
0.8882	High Similarity	NPC288152
0.8882	High Similarity	NPC470716
0.8882	High Similarity	NPC137871
0.8882	High Similarity	NPC11847
0.8882	High Similarity	NPC93619
0.8882	High Similarity	NPC101399
0.8882	High Similarity	NPC9002
0.8882	High Similarity	NPC474522
0.8882	High Similarity	NPC470715
0.8882	High Similarity	NPC257011
0.8882	High Similarity	NPC221288
0.8869	High Similarity	NPC260504
0.8869	High Similarity	NPC473278
0.8869	High Similarity	NPC89809
0.8862	High Similarity	NPC80068
0.8857	High Similarity	NPC470719
0.8857	High Similarity	NPC295625
0.8857	High Similarity	NPC473554
0.8857	High Similarity	NPC33083
0.8851	High Similarity	NPC470447
0.8851	High Similarity	NPC470449
0.8851	High Similarity	NPC470446
0.8851	High Similarity	NPC470445
0.8851	High Similarity	NPC199172
0.8851	High Similarity	NPC35924
0.8844	High Similarity	NPC471030
0.8837	High Similarity	NPC231787
0.883	High Similarity	NPC172033
0.883	High Similarity	NPC175230
0.883	High Similarity	NPC88560
0.8824	High Similarity	NPC204937
0.8824	High Similarity	NPC92815
0.8824	High Similarity	NPC149011
0.8824	High Similarity	NPC210808
0.8824	High Similarity	NPC199079
0.8817	High Similarity	NPC103633
0.8814	High Similarity	NPC314672
0.881	High Similarity	NPC11608
0.881	High Similarity	NPC205824
0.881	High Similarity	NPC85751
0.881	High Similarity	NPC139060
0.881	High Similarity	NPC129264
0.881	High Similarity	NPC297404
0.881	High Similarity	NPC19240
0.8807	High Similarity	NPC65489
0.8802	High Similarity	NPC90905
0.8802	High Similarity	NPC4013
0.88	High Similarity	NPC231254
0.8786	High Similarity	NPC139571
0.8786	High Similarity	NPC217520
0.8779	High Similarity	NPC115760
0.8779	High Similarity	NPC101191
0.8779	High Similarity	NPC210094
0.8779	High Similarity	NPC477848
0.8779	High Similarity	NPC237435
0.8779	High Similarity	NPC49344
0.8779	High Similarity	NPC43211
0.8779	High Similarity	NPC264735
0.8779	High Similarity	NPC253685
0.8779	High Similarity	NPC135277
0.8772	High Similarity	NPC47140
0.8772	High Similarity	NPC67134
0.8765	High Similarity	NPC137460
0.8765	High Similarity	NPC658
0.8765	High Similarity	NPC197708
0.875	High Similarity	NPC261623
0.875	High Similarity	NPC111490
0.8743	High Similarity	NPC210961
0.8743	High Similarity	NPC477628
0.8743	High Similarity	NPC472994
0.8743	High Similarity	NPC71780
0.8743	High Similarity	NPC195685
0.8743	High Similarity	NPC477629
0.8743	High Similarity	NPC270675
0.8736	High Similarity	NPC473682
0.8736	High Similarity	NPC470443
0.8736	High Similarity	NPC473571
0.8736	High Similarity	NPC110941
0.8736	High Similarity	NPC470444
0.8736	High Similarity	NPC241423
0.8736	High Similarity	NPC126784
0.8728	High Similarity	NPC211532
0.8728	High Similarity	NPC472384
0.8728	High Similarity	NPC89127
0.8728	High Similarity	NPC473862
0.8728	High Similarity	NPC472385
0.8728	High Similarity	NPC471669
0.8728	High Similarity	NPC472382
0.8728	High Similarity	NPC233994
0.8728	High Similarity	NPC296018
0.8728	High Similarity	NPC268533
0.8728	High Similarity	NPC472380
0.8728	High Similarity	NPC169733
0.8728	High Similarity	NPC65563
0.8728	High Similarity	NPC198324
0.8728	High Similarity	NPC470949
0.8728	High Similarity	NPC154741
0.8728	High Similarity	NPC8573
0.8721	High Similarity	NPC472993
0.8721	High Similarity	NPC163165
0.8713	High Similarity	NPC245014
0.8713	High Similarity	NPC76047
0.8713	High Similarity	NPC175429
0.8713	High Similarity	NPC282987
0.8713	High Similarity	NPC155763
0.8713	High Similarity	NPC84265
0.8713	High Similarity	NPC277532
0.8713	High Similarity	NPC209550
0.8713	High Similarity	NPC138990
0.8713	High Similarity	NPC235260
0.8713	High Similarity	NPC20505
0.8708	High Similarity	NPC31208
0.8708	High Similarity	NPC93065
0.8708	High Similarity	NPC472724
0.8708	High Similarity	NPC160543
0.8708	High Similarity	NPC469652
0.8708	High Similarity	NPC472720
0.8708	High Similarity	NPC472721

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 NPC470438 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	368
0.1-0.2	942
0.2-0.3	1989
0.3-0.4	2653
0.4-0.5	1895
0.5-0.6	891
0.6-0.7	286
0.7-0.8	93
0.8-0.85	27
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8914	High Similarity	NPD7879	Clinical (unspecified phase)
0.8779	High Similarity	NPD4338	Clinical (unspecified phase)
0.8671	High Similarity	NPD7808	Phase 3
0.8613	High Similarity	NPD7251	Discontinued
0.8555	High Similarity	NPD6797	Phase 2
0.8555	High Similarity	NPD7993	Clinical (unspecified phase)
0.8514	High Similarity	NPD8313	Approved
0.8514	High Similarity	NPD8312	Approved
0.8497	Intermediate Similarity	NPD7472	Approved
0.8452	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8439	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8439	Intermediate Similarity	NPD7054	Approved
0.8391	Intermediate Similarity	NPD7074	Phase 3
0.8382	Intermediate Similarity	NPD3751	Discontinued
0.8333	Intermediate Similarity	NPD7435	Discontinued
0.8333	Intermediate Similarity	NPD5402	Approved
0.8284	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD3818	Discontinued
0.8266	Intermediate Similarity	NPD6166	Phase 2
0.8266	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8256	Intermediate Similarity	NPD3787	Discontinued
0.8191	Intermediate Similarity	NPD7871	Phase 2
0.8191	Intermediate Similarity	NPD7870	Phase 2
0.8172	Intermediate Similarity	NPD6781	Approved
0.8172	Intermediate Similarity	NPD6778	Approved
0.8172	Intermediate Similarity	NPD6779	Approved
0.8172	Intermediate Similarity	NPD6782	Approved
0.8172	Intermediate Similarity	NPD6776	Approved
0.8172	Intermediate Similarity	NPD6780	Approved
0.8172	Intermediate Similarity	NPD6777	Approved
0.8168	Intermediate Similarity	NPD7874	Approved
0.8168	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD7697	Approved
0.8138	Intermediate Similarity	NPD7696	Phase 3
0.8138	Intermediate Similarity	NPD7698	Approved
0.8129	Intermediate Similarity	NPD7075	Discontinued
0.8063	Intermediate Similarity	NPD7701	Phase 2
0.8059	Intermediate Similarity	NPD8455	Phase 2
0.7989	Intermediate Similarity	NPD6559	Discontinued
0.7978	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7968	Intermediate Similarity	NPD7700	Phase 2
0.7968	Intermediate Similarity	NPD7699	Phase 2
0.7953	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD7801	Approved
0.7927	Intermediate Similarity	NPD8151	Discontinued
0.7917	Intermediate Similarity	NPD5403	Approved
0.7912	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD3817	Phase 2
0.7903	Intermediate Similarity	NPD6535	Approved
0.7903	Intermediate Similarity	NPD6534	Approved
0.7889	Intermediate Similarity	NPD7685	Pre-registration
0.7882	Intermediate Similarity	NPD4380	Phase 2
0.7869	Intermediate Similarity	NPD8434	Phase 2
0.785	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD2801	Approved
0.7831	Intermediate Similarity	NPD6190	Approved
0.7821	Intermediate Similarity	NPD5844	Phase 1
0.7812	Intermediate Similarity	NPD8320	Phase 1
0.7812	Intermediate Similarity	NPD8319	Approved
0.7798	Intermediate Similarity	NPD5401	Approved
0.7791	Intermediate Similarity	NPD1934	Approved
0.7791	Intermediate Similarity	NPD6801	Discontinued
0.7772	Intermediate Similarity	NPD8150	Discontinued
0.7765	Intermediate Similarity	NPD1653	Approved
0.7759	Intermediate Similarity	NPD3882	Suspended
0.7755	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD7783	Phase 2
0.7753	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7819	Suspended
0.7746	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6799	Approved
0.7733	Intermediate Similarity	NPD7411	Suspended
0.7708	Intermediate Similarity	NPD6823	Phase 2
0.7701	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1512	Approved
0.7611	Intermediate Similarity	NPD7473	Discontinued
0.7584	Intermediate Similarity	NPD6959	Discontinued
0.7557	Intermediate Similarity	NPD7768	Phase 2
0.7545	Intermediate Similarity	NPD1549	Phase 2
0.7542	Intermediate Similarity	NPD6232	Discontinued
0.7529	Intermediate Similarity	NPD1511	Approved
0.7528	Intermediate Similarity	NPD5494	Approved
0.7514	Intermediate Similarity	NPD3749	Approved
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7228	Approved
0.7471	Intermediate Similarity	NPD6599	Discontinued
0.7456	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD1465	Phase 2
0.7414	Intermediate Similarity	NPD7458	Discontinued
0.7403	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7199	Phase 2
0.7384	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD6213	Phase 3
0.7382	Intermediate Similarity	NPD6212	Phase 3
0.7382	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7266	Discontinued
0.7358	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4628	Phase 3
0.7326	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1551	Phase 2
0.7321	Intermediate Similarity	NPD2935	Discontinued
0.7314	Intermediate Similarity	NPD3226	Approved
0.7289	Intermediate Similarity	NPD1933	Approved
0.7273	Intermediate Similarity	NPD6233	Phase 2
0.7262	Intermediate Similarity	NPD1510	Phase 2
0.7251	Intermediate Similarity	NPD3750	Approved
0.7238	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD8059	Phase 3
0.7219	Intermediate Similarity	NPD7240	Approved
0.7219	Intermediate Similarity	NPD2796	Approved
0.7216	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7097	Phase 1
0.72	Intermediate Similarity	NPD7584	Approved
0.7191	Intermediate Similarity	NPD37	Approved
0.7186	Intermediate Similarity	NPD447	Suspended
0.7182	Intermediate Similarity	NPD6234	Discontinued
0.7167	Intermediate Similarity	NPD4965	Approved
0.7167	Intermediate Similarity	NPD4967	Phase 2
0.7167	Intermediate Similarity	NPD4966	Approved
0.712	Intermediate Similarity	NPD3926	Phase 2
0.7117	Intermediate Similarity	NPD1203	Approved
0.7108	Intermediate Similarity	NPD6798	Discontinued
0.7108	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6844	Discontinued
0.7091	Intermediate Similarity	NPD6832	Phase 2
0.7083	Intermediate Similarity	NPD230	Phase 1
0.7081	Intermediate Similarity	NPD1091	Approved
0.7079	Intermediate Similarity	NPD7585	Approved
0.7059	Intermediate Similarity	NPD7033	Discontinued
0.7053	Intermediate Similarity	NPD8404	Phase 2
0.7035	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7583	Approved
0.7024	Intermediate Similarity	NPD1240	Approved
0.7011	Intermediate Similarity	NPD1247	Approved
0.7006	Intermediate Similarity	NPD2313	Discontinued
0.6995	Remote Similarity	NPD919	Approved
0.6989	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD5953	Discontinued
0.6982	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2346	Discontinued
0.6959	Remote Similarity	NPD3748	Approved
0.6954	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD8368	Discontinued
0.6941	Remote Similarity	NPD1607	Approved
0.6935	Remote Similarity	NPD8285	Discontinued
0.6923	Remote Similarity	NPD1613	Approved
0.6923	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD8127	Discontinued
0.6915	Remote Similarity	NPD7799	Discontinued
0.69	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD2532	Approved
0.6893	Remote Similarity	NPD2534	Approved
0.6893	Remote Similarity	NPD2533	Approved
0.6882	Remote Similarity	NPD6355	Discontinued
0.6881	Remote Similarity	NPD7680	Approved
0.6879	Remote Similarity	NPD2344	Approved
0.6878	Remote Similarity	NPD7286	Phase 2
0.6875	Remote Similarity	NPD7930	Approved
0.6872	Remote Similarity	NPD8361	Approved
0.6872	Remote Similarity	NPD8360	Approved
0.686	Remote Similarity	NPD2799	Discontinued
0.6848	Remote Similarity	NPD3225	Approved
0.6839	Remote Similarity	NPD8407	Phase 2
0.6829	Remote Similarity	NPD9717	Approved
0.6824	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD943	Approved
0.6821	Remote Similarity	NPD6100	Approved
0.6821	Remote Similarity	NPD6099	Approved
0.6816	Remote Similarity	NPD920	Approved
0.6805	Remote Similarity	NPD3764	Approved
0.6798	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD8435	Approved
0.6776	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD4308	Phase 3
0.676	Remote Similarity	NPD6273	Approved
0.675	Remote Similarity	NPD8485	Approved
0.6746	Remote Similarity	NPD7095	Approved
0.6742	Remote Similarity	NPD7390	Discontinued
0.6739	Remote Similarity	NPD5353	Approved
0.6737	Remote Similarity	NPD7177	Discontinued
0.6736	Remote Similarity	NPD7549	Discontinued
0.6724	Remote Similarity	NPD5404	Approved
0.6724	Remote Similarity	NPD5405	Approved
0.6724	Remote Similarity	NPD5406	Approved
0.6724	Remote Similarity	NPD5408	Approved
0.6723	Remote Similarity	NPD2354	Approved
0.6723	Remote Similarity	NPD3887	Approved
0.6723	Remote Similarity	NPD2309	Approved
0.6706	Remote Similarity	NPD3268	Approved
0.6706	Remote Similarity	NPD411	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