NPASS Compound

Structure

CID66504 OpenBabel06191715402D 30 32 0 0 1 0 0 0 0 0999 V2000 -5.6304 -6.2532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9362 -6.6133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6002 3.8373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7592 2.5501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0248 -3.8157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4714 -4.9660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0650 2.1900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3614 -3.3698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8966 -1.7226 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 -4.6793 -5.9442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8081 2.8592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6939 -3.0725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1535 -2.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -2.0827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5204 -4.6570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2729 1.2119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -1.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7377 -0.4354 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 2.6720 -3.2804 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7772 -5.3261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2240 0.9029 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3125 -3.6789 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6887 -0.7444 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 1.3849 -2.1215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5298 0.5427 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 6 12 1 0 0 0 0 6 18 1 0 0 0 0 7 13 1 0 0 0 0 7 19 1 0 0 0 0 8 17 1 0 0 0 0 9 15 1 0 0 0 0 9 26 1 0 0 0 0 10 15 2 0 0 0 0 10 27 1 0 0 0 0 11 28 1 0 0 0 0 14 23 2 0 0 0 0 14 29 1 0 0 0 0 15 16 1 0 0 0 0 16 8 1 6 0 0 0 16 20 1 0 0 0 0 17 22 1 1 0 0 0 17 29 1 0 0 0 0 18 24 2 0 0 0 0 18 26 1 0 0 0 0 19 25 2 0 0 0 0 19 30 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 6 0 0 0 21 27 1 0 0 0 0 21 30 1 1 0 0 0 22 11 1 1 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.21
Volume:	423.175
LogP:	3.296
LogD:	2.479
LogS:	-4.245
# Rotatable Bonds:	11
TPSA:	100.66
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.333
Synthetic Accessibility Score:	4.941
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.606
MDCK Permeability:	5.685177893610671e-05
Pgp-inhibitor:	0.66
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.934
Plasma Protein Binding (PPB):	70.90858459472656%
Volume Distribution (VD):	1.133
Pgp-substrate:	33.65785217285156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.099
CYP1A2-substrate:	0.031
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.195
CYP2C9-inhibitor:	0.193
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.085
CYP2D6-substrate:	0.04
CYP3A4-inhibitor:	0.525
CYP3A4-substrate:	0.287

ADMET: Excretion

Clearance (CL):	8.623
Half-life (T1/2):	0.765

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.67
Drug-inuced Liver Injury (DILI):	0.926
AMES Toxicity:	0.992
Rat Oral Acute Toxicity:	0.42
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.68
Carcinogencity:	0.956
Eye Corrosion:	0.194
Eye Irritation:	0.234
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC66504

Natural Product ID:	NPC66504
*Common Name:**	Didrovaltrate
IUPAC Name:	[(1S,4aS,6S,7R,7aS)-6-acetyloxy-1-(3-methylbutanoyloxy)spiro[4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-7,2'-oxirane]-4-yl]methyl 3-methylbutanoate
Synonyms:	Didrovaltrate
Standard InCHIKey:	PHHROXLDZHUIGO-PNBTUHDLSA-N
Standard InCHI:	InChI=1S/C22H32O8/c1-12(2)6-18(24)26-9-15-10-27-21(30-19(25)7-13(3)4)20-16(15)8-17(29-14(5)23)22(20)11-28-22/h10,12-13,16-17,20-21H,6-9,11H2,1-5H3/t16-,17+,20-,21+,22-/m1/s1
SMILES:	CC(CC(=O)OCC1=CO[C@H]([C@H]2[C@@H]1C[C@@H]([C@@]12CO1)OC(=O)C)OC(=O)CC(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL550227
PubChem CID:	65689
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001565] Iridoids and derivatives

*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
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	roots	n.a.	n.a.	PMID[12398547]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	root	n.a.	PMID[18164718]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19245261]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20151678]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20853876]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20853876]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	root	n.a.	PMID[547813]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	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	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[464849]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	6600.0	nM	PMID[464849]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	7500.0	nM	PMID[464849]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3800.0	nM	PMID[464849]

☑ 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 NPC66504 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	260
0.1-0.2	2396
0.2-0.3	7784
0.3-0.4	15663
0.4-0.5	8669
0.5-0.6	6542
0.6-0.7	1265
0.7-0.8	98
0.8-0.85	3
0.85-0.9	10
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9444	High Similarity	NPC86843
0.9333	High Similarity	NPC284063
0.9326	High Similarity	NPC274588
0.9222	High Similarity	NPC93869
0.9222	High Similarity	NPC6765
0.914	High Similarity	NPC476228
0.9121	High Similarity	NPC170527
0.8947	High Similarity	NPC329834
0.883	High Similarity	NPC476320
0.883	High Similarity	NPC476211
0.8737	High Similarity	NPC476230
0.8737	High Similarity	NPC216911
0.8737	High Similarity	NPC27474
0.8557	High Similarity	NPC329704
0.8478	Intermediate Similarity	NPC235051
0.8404	Intermediate Similarity	NPC291709
0.8404	Intermediate Similarity	NPC241407
0.8333	Intermediate Similarity	NPC90819
0.8333	Intermediate Similarity	NPC124181
0.8235	Intermediate Similarity	NPC193741
0.8229	Intermediate Similarity	NPC153559
0.8182	Intermediate Similarity	NPC37240
0.8144	Intermediate Similarity	NPC473307
0.8137	Intermediate Similarity	NPC208307
0.8081	Intermediate Similarity	NPC177013
0.8081	Intermediate Similarity	NPC35185
0.8081	Intermediate Similarity	NPC4899
0.8081	Intermediate Similarity	NPC474730
0.8077	Intermediate Similarity	NPC475851
0.8077	Intermediate Similarity	NPC475924
0.802	Intermediate Similarity	NPC170432
0.8	Intermediate Similarity	NPC475928
0.7959	Intermediate Similarity	NPC151093
0.7957	Intermediate Similarity	NPC233997
0.7941	Intermediate Similarity	NPC148270
0.7941	Intermediate Similarity	NPC80338
0.7941	Intermediate Similarity	NPC197813
0.7935	Intermediate Similarity	NPC471480
0.7879	Intermediate Similarity	NPC244878
0.7865	Intermediate Similarity	NPC475946
0.7864	Intermediate Similarity	NPC110701
0.7835	Intermediate Similarity	NPC167893
0.78	Intermediate Similarity	NPC4637
0.78	Intermediate Similarity	NPC287539
0.78	Intermediate Similarity	NPC3488
0.78	Intermediate Similarity	NPC219038
0.78	Intermediate Similarity	NPC20673
0.78	Intermediate Similarity	NPC98859
0.7723	Intermediate Similarity	NPC471599
0.7723	Intermediate Similarity	NPC106668
0.767	Intermediate Similarity	NPC127235
0.7647	Intermediate Similarity	NPC27687
0.7629	Intermediate Similarity	NPC470187
0.7553	Intermediate Similarity	NPC137253
0.7526	Intermediate Similarity	NPC294643
0.7526	Intermediate Similarity	NPC274274
0.7526	Intermediate Similarity	NPC473150
0.75	Intermediate Similarity	NPC304445
0.75	Intermediate Similarity	NPC22918
0.75	Intermediate Similarity	NPC261372
0.75	Intermediate Similarity	NPC263674
0.75	Intermediate Similarity	NPC236580
0.75	Intermediate Similarity	NPC58267
0.75	Intermediate Similarity	NPC50464
0.75	Intermediate Similarity	NPC93190
0.7451	Intermediate Similarity	NPC471767
0.7426	Intermediate Similarity	NPC96399
0.7426	Intermediate Similarity	NPC117066
0.7426	Intermediate Similarity	NPC469919
0.7426	Intermediate Similarity	NPC469918
0.7396	Intermediate Similarity	NPC148534
0.7379	Intermediate Similarity	NPC304163
0.7379	Intermediate Similarity	NPC250594
0.7379	Intermediate Similarity	NPC214714
0.7379	Intermediate Similarity	NPC200672
0.7374	Intermediate Similarity	NPC281775
0.7347	Intermediate Similarity	NPC276298
0.7333	Intermediate Similarity	NPC470980
0.732	Intermediate Similarity	NPC472872
0.7308	Intermediate Similarity	NPC473148
0.7292	Intermediate Similarity	NPC258501
0.7282	Intermediate Similarity	NPC67296
0.7282	Intermediate Similarity	NPC26557
0.7255	Intermediate Similarity	NPC223700
0.7255	Intermediate Similarity	NPC249171
0.7255	Intermediate Similarity	NPC49833
0.7228	Intermediate Similarity	NPC474297
0.7228	Intermediate Similarity	NPC113433
0.7228	Intermediate Similarity	NPC161293
0.7212	Intermediate Similarity	NPC475956
0.7212	Intermediate Similarity	NPC252242
0.72	Intermediate Similarity	NPC63897
0.7184	Intermediate Similarity	NPC130792
0.7184	Intermediate Similarity	NPC186861
0.7157	Intermediate Similarity	NPC472290
0.7157	Intermediate Similarity	NPC474182
0.7143	Intermediate Similarity	NPC232515
0.7143	Intermediate Similarity	NPC260809
0.7143	Intermediate Similarity	NPC474783
0.7143	Intermediate Similarity	NPC186109
0.7117	Intermediate Similarity	NPC106446
0.71	Intermediate Similarity	NPC472874
0.7097	Intermediate Similarity	NPC474739
0.7087	Intermediate Similarity	NPC79449
0.7087	Intermediate Similarity	NPC474957
0.7087	Intermediate Similarity	NPC37866
0.7087	Intermediate Similarity	NPC45125
0.7071	Intermediate Similarity	NPC246173
0.7065	Intermediate Similarity	NPC264610
0.7053	Intermediate Similarity	NPC257358
0.7053	Intermediate Similarity	NPC474472
0.7048	Intermediate Similarity	NPC470972
0.7048	Intermediate Similarity	NPC80144
0.7048	Intermediate Similarity	NPC49393
0.7048	Intermediate Similarity	NPC78127
0.7048	Intermediate Similarity	NPC471757
0.7048	Intermediate Similarity	NPC475986
0.7027	Intermediate Similarity	NPC287075
0.7019	Intermediate Similarity	NPC473146
0.7019	Intermediate Similarity	NPC98813
0.7019	Intermediate Similarity	NPC471381
0.7019	Intermediate Similarity	NPC13743
0.7018	Intermediate Similarity	NPC219656
0.701	Intermediate Similarity	NPC149018
0.701	Intermediate Similarity	NPC171484
0.7009	Intermediate Similarity	NPC85670
0.7	Intermediate Similarity	NPC155215
0.699	Remote Similarity	NPC470684
0.699	Remote Similarity	NPC347923
0.699	Remote Similarity	NPC470683
0.699	Remote Similarity	NPC476057
0.699	Remote Similarity	NPC113976
0.699	Remote Similarity	NPC198549
0.6979	Remote Similarity	NPC98276
0.6979	Remote Similarity	NPC259296
0.697	Remote Similarity	NPC283409
0.6961	Remote Similarity	NPC240838
0.6961	Remote Similarity	NPC472873
0.6939	Remote Similarity	NPC74139
0.6939	Remote Similarity	NPC31349
0.6939	Remote Similarity	NPC270270
0.6931	Remote Similarity	NPC320089
0.6931	Remote Similarity	NPC258216
0.6931	Remote Similarity	NPC474835
0.6923	Remote Similarity	NPC274458
0.6923	Remote Similarity	NPC472015
0.6923	Remote Similarity	NPC279561
0.6916	Remote Similarity	NPC86095
0.6909	Remote Similarity	NPC106760
0.6907	Remote Similarity	NPC149725
0.6907	Remote Similarity	NPC304509
0.6907	Remote Similarity	NPC47958
0.69	Remote Similarity	NPC65665
0.69	Remote Similarity	NPC117596
0.69	Remote Similarity	NPC216826
0.69	Remote Similarity	NPC470573
0.69	Remote Similarity	NPC270908
0.69	Remote Similarity	NPC120021
0.69	Remote Similarity	NPC231710
0.69	Remote Similarity	NPC475748
0.6897	Remote Similarity	NPC233500
0.6893	Remote Similarity	NPC54731
0.6893	Remote Similarity	NPC98165
0.6887	Remote Similarity	NPC222062
0.6887	Remote Similarity	NPC94919
0.6887	Remote Similarity	NPC105725
0.6881	Remote Similarity	NPC473517
0.6875	Remote Similarity	NPC474266
0.6875	Remote Similarity	NPC127917
0.6869	Remote Similarity	NPC224652
0.6869	Remote Similarity	NPC471149
0.6869	Remote Similarity	NPC473151
0.6869	Remote Similarity	NPC79549
0.6857	Remote Similarity	NPC255677
0.6857	Remote Similarity	NPC306344
0.6857	Remote Similarity	NPC22149
0.6852	Remote Similarity	NPC41681
0.6852	Remote Similarity	NPC470979
0.6852	Remote Similarity	NPC470975
0.6852	Remote Similarity	NPC291414
0.6852	Remote Similarity	NPC475290
0.6852	Remote Similarity	NPC103088
0.6852	Remote Similarity	NPC44004
0.6852	Remote Similarity	NPC54737
0.6847	Remote Similarity	NPC475495
0.6842	Remote Similarity	NPC290693
0.6838	Remote Similarity	NPC196130
0.6837	Remote Similarity	NPC204048
0.6837	Remote Similarity	NPC261253
0.6837	Remote Similarity	NPC474045
0.6837	Remote Similarity	NPC304558
0.6837	Remote Similarity	NPC470657
0.6837	Remote Similarity	NPC469676
0.6832	Remote Similarity	NPC472124
0.6832	Remote Similarity	NPC472126
0.6832	Remote Similarity	NPC472125
0.6832	Remote Similarity	NPC122057
0.6827	Remote Similarity	NPC471150
0.6827	Remote Similarity	NPC182811
0.6822	Remote Similarity	NPC197541

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 NPC66504 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	3070
0.2-0.3	3781
0.3-0.4	1440
0.4-0.5	396
0.5-0.6	177
0.6-0.7	13
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6897	Remote Similarity	NPD7503	Approved
0.6875	Remote Similarity	NPD8133	Approved
0.6638	Remote Similarity	NPD7327	Approved
0.6638	Remote Similarity	NPD7328	Approved
0.6634	Remote Similarity	NPD1695	Approved
0.6581	Remote Similarity	NPD7516	Approved
0.6577	Remote Similarity	NPD6686	Approved
0.6569	Remote Similarity	NPD46	Approved
0.6569	Remote Similarity	NPD6698	Approved
0.6529	Remote Similarity	NPD7507	Approved
0.6525	Remote Similarity	NPD8377	Approved
0.6525	Remote Similarity	NPD8294	Approved
0.6491	Remote Similarity	NPD6053	Discontinued
0.6471	Remote Similarity	NPD8380	Approved
0.6471	Remote Similarity	NPD8296	Approved
0.6471	Remote Similarity	NPD8379	Approved
0.6471	Remote Similarity	NPD8335	Approved
0.6471	Remote Similarity	NPD8378	Approved
0.6471	Remote Similarity	NPD8033	Approved
0.6436	Remote Similarity	NPD4250	Approved
0.6436	Remote Similarity	NPD4251	Approved
0.6408	Remote Similarity	NPD7838	Discovery
0.64	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD7319	Approved
0.6339	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6412	Phase 2
0.6337	Remote Similarity	NPD4249	Approved
0.6296	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD6371	Approved
0.6154	Remote Similarity	NPD6051	Approved
0.6091	Remote Similarity	NPD6648	Approved
0.608	Remote Similarity	NPD8293	Discontinued
0.6066	Remote Similarity	NPD8513	Phase 3
0.6061	Remote Similarity	NPD4819	Approved
0.6061	Remote Similarity	NPD4822	Approved
0.6061	Remote Similarity	NPD4821	Approved
0.6061	Remote Similarity	NPD4820	Approved
0.6061	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD5344	Discontinued
0.6032	Remote Similarity	NPD7736	Approved
0.6016	Remote Similarity	NPD6370	Approved
0.6	Remote Similarity	NPD7638	Approved
0.5965	Remote Similarity	NPD6008	Approved
0.5946	Remote Similarity	NPD7639	Approved
0.5946	Remote Similarity	NPD7640	Approved
0.5941	Remote Similarity	NPD6435	Approved
0.5935	Remote Similarity	NPD8516	Approved
0.5935	Remote Similarity	NPD8515	Approved
0.5935	Remote Similarity	NPD8517	Approved
0.592	Remote Similarity	NPD7492	Approved
0.5913	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5362	Discontinued
0.5882	Remote Similarity	NPD7154	Phase 3
0.5877	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD6616	Approved
0.5859	Remote Similarity	NPD4271	Approved
0.5859	Remote Similarity	NPD4268	Approved
0.5854	Remote Similarity	NPD6054	Approved
0.5854	Remote Similarity	NPD6059	Approved
0.5843	Remote Similarity	NPD1145	Discontinued
0.5827	Remote Similarity	NPD7078	Approved
0.5798	Remote Similarity	NPD6882	Approved
0.5781	Remote Similarity	NPD8336	Approved
0.5781	Remote Similarity	NPD8337	Approved
0.5763	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD5368	Approved
0.5741	Remote Similarity	NPD7637	Suspended
0.5741	Remote Similarity	NPD5693	Phase 1
0.5741	Remote Similarity	NPD7983	Approved
0.5738	Remote Similarity	NPD7115	Discovery
0.5738	Remote Similarity	NPD6009	Approved
0.5738	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD3669	Approved
0.5728	Remote Similarity	NPD5332	Approved
0.5728	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD5331	Approved
0.5726	Remote Similarity	NPD6319	Approved
0.5714	Remote Similarity	NPD7146	Approved
0.5714	Remote Similarity	NPD6684	Approved
0.5714	Remote Similarity	NPD6409	Approved
0.5714	Remote Similarity	NPD7521	Approved
0.5714	Remote Similarity	NPD5330	Approved
0.5714	Remote Similarity	NPD7334	Approved
0.57	Remote Similarity	NPD4802	Phase 2
0.57	Remote Similarity	NPD4238	Approved
0.5686	Remote Similarity	NPD4790	Discontinued
0.5686	Remote Similarity	NPD5369	Approved
0.568	Remote Similarity	NPD6015	Approved
0.568	Remote Similarity	NPD6016	Approved
0.5678	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5667	Remote Similarity	NPD8297	Approved
0.566	Remote Similarity	NPD7524	Approved
0.5648	Remote Similarity	NPD3168	Discontinued
0.5635	Remote Similarity	NPD5988	Approved
0.5625	Remote Similarity	NPD6083	Phase 2
0.5625	Remote Similarity	NPD6084	Phase 2
0.5607	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD6903	Approved
0.5606	Remote Similarity	NPD8338	Approved
0.5603	Remote Similarity	NPD8170	Clinical (unspecified phase)

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