NPASS Compound

Structure

NPC475768 OpenBabel07101719142D 31 35 0 0 1 0 0 0 0 0999 V2000 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -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 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 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 0.8660 0.5000 0.0000 C 0 0 2 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 1 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 1 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 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 2 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 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 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 -3.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 -3.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 8 2 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 29 1 0 0 0 0 7 30 1 0 0 0 0 8 21 1 0 0 0 0 9 12 1 0 0 0 0 10 18 2 0 0 0 0 10 29 1 0 0 0 0 11 9 1 6 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 14 2 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 1 0 0 0 14 18 1 0 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 15 24 1 6 0 0 0 16 17 1 0 0 0 0 16 25 1 6 0 0 0 17 19 1 0 0 0 0 17 26 1 1 0 0 0 18 30 1 0 0 0 0 19 31 1 6 0 0 0 20 22 2 0 0 0 0 20 27 1 0 0 0 0 21 28 2 0 0 0 0 21 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	429.11
Volume:	398.007
LogP:	0.984
LogD:	0.912
LogS:	-1.704
# Rotatable Bonds:	3
TPSA:	154.78
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.403
Synthetic Accessibility Score:	4.225
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.061
MDCK Permeability:	1.357655582978623e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.025
Human Intestinal Absorption (HIA):	0.043
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.933

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.332
Plasma Protein Binding (PPB):	91.71656036376953%
Volume Distribution (VD):	0.782
Pgp-substrate:	8.132051467895508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.199
CYP1A2-substrate:	0.055
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.074
CYP2C9-inhibitor:	0.158
CYP2C9-substrate:	0.675
CYP2D6-inhibitor:	0.327
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.763
CYP3A4-substrate:	0.076

ADMET: Excretion

Clearance (CL):	6.319
Half-life (T1/2):	0.805

ADMET: Toxicity

hERG Blockers:	0.088
Human Hepatotoxicity (H-HT):	0.204
Drug-inuced Liver Injury (DILI):	0.918
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.037
Carcinogencity:	0.198
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.057

Download Data

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

Natural Product: NPC475768

Natural Product ID:	NPC475768
*Common Name:**	Phenpanstatin
IUPAC Name:	[(1R,2R,3S,4S,4aR,11bR)-2,3,4,7-tetrahydroxy-6-oxo-2,3,4,4a,5,11b-hexahydro-1H-[1,3]dioxolo[4,5-j]phenanthridin-1-yl] benzoate
Synonyms:	Phenpanstatin
Standard InCHIKey:	DJJSHXTUGRWWMI-QUVFKJLXSA-N
Standard InCHI:	InChI=1S/C21H19NO9/c23-14-12-9(6-10-18(14)30-7-29-10)11-13(22-20(12)27)15(24)16(25)17(26)19(11)31-21(28)8-4-2-1-3-5-8/h1-6,11,13,15-17,19,23-26H,7H2,(H,22,27)/t11-,13-,15+,16+,17-,19-/m1/s1
SMILES:	C1OC2=C(O1)C(=C3C(=C2)C4C(C(C(C(C4OC(=O)C5=CC=CC=C5)O)O)O)NC3=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515014
PubChem CID:	10502697
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004129] Phenanthridine- and phenanthridone-type amaryllidaceae alkaloids

*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
NPO33437	amaryllidaceae	Family	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22921081]

☑ 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
ED50	1
GI50	6
IC50	1

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	0.00021	ug.mL-1	PMID[515528]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	=	0.00037	ug.mL-1	PMID[515528]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	0.0001	ug.mL-1	PMID[515528]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	0.00055	ug.mL-1	PMID[515528]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	0.00031	ug.mL-1	PMID[515528]
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	=	0.0019	ug.mL-1	PMID[515528]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.0016	ug ml-1	PMID[515528]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	0.23	nM	PMID[515529]

☑ 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 NPC475768 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	306
0.1-0.2	1310
0.2-0.3	4057
0.3-0.4	10517
0.4-0.5	7552
0.5-0.6	6724
0.6-0.7	10160
0.7-0.8	2050
0.8-0.85	14
0.85-0.9	6
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8791	High Similarity	NPC1291
0.8791	High Similarity	NPC115343
0.875	High Similarity	NPC474607
0.8703	High Similarity	NPC474650
0.8681	High Similarity	NPC110374
0.8681	High Similarity	NPC289743
0.8663	High Similarity	NPC474661
0.8663	High Similarity	NPC475919
0.8595	High Similarity	NPC475794
0.8361	Intermediate Similarity	NPC304846
0.8315	Intermediate Similarity	NPC182257
0.8251	Intermediate Similarity	NPC89199
0.8251	Intermediate Similarity	NPC54125
0.8177	Intermediate Similarity	NPC474009
0.8128	Intermediate Similarity	NPC311912
0.8085	Intermediate Similarity	NPC88557
0.8075	Intermediate Similarity	NPC474953
0.8	Intermediate Similarity	NPC470642
0.7931	Intermediate Similarity	NPC80472
0.7895	Intermediate Similarity	NPC474051
0.7884	Intermediate Similarity	NPC118162
0.7884	Intermediate Similarity	NPC83049
0.7884	Intermediate Similarity	NPC320471
0.7876	Intermediate Similarity	NPC473713
0.7846	Intermediate Similarity	NPC18306
0.7842	Intermediate Similarity	NPC79322
0.7838	Intermediate Similarity	NPC69360
0.7819	Intermediate Similarity	NPC198741
0.7812	Intermediate Similarity	NPC469506
0.7778	Intermediate Similarity	NPC121290
0.7755	Intermediate Similarity	NPC208797
0.7755	Intermediate Similarity	NPC170203
0.7755	Intermediate Similarity	NPC53680
0.7755	Intermediate Similarity	NPC34780
0.775	Intermediate Similarity	NPC33256
0.7725	Intermediate Similarity	NPC42797
0.7725	Intermediate Similarity	NPC473445
0.7718	Intermediate Similarity	NPC11708
0.7713	Intermediate Similarity	NPC150943
0.7713	Intermediate Similarity	NPC24627
0.7713	Intermediate Similarity	NPC91634
0.7713	Intermediate Similarity	NPC268718
0.7708	Intermediate Similarity	NPC117911
0.7696	Intermediate Similarity	NPC2173
0.7696	Intermediate Similarity	NPC119818
0.7696	Intermediate Similarity	NPC202771
0.7696	Intermediate Similarity	NPC328700
0.7692	Intermediate Similarity	NPC196771
0.7692	Intermediate Similarity	NPC472723
0.7692	Intermediate Similarity	NPC297574
0.7684	Intermediate Similarity	NPC291977
0.7684	Intermediate Similarity	NPC14294
0.7684	Intermediate Similarity	NPC116759
0.7672	Intermediate Similarity	NPC258322
0.7672	Intermediate Similarity	NPC319749
0.7672	Intermediate Similarity	NPC191352
0.766	Intermediate Similarity	NPC230531
0.766	Intermediate Similarity	NPC215400
0.7641	Intermediate Similarity	NPC171706
0.7641	Intermediate Similarity	NPC469354
0.7641	Intermediate Similarity	NPC84482
0.7641	Intermediate Similarity	NPC169645
0.7641	Intermediate Similarity	NPC193377
0.7632	Intermediate Similarity	NPC22324
0.7632	Intermediate Similarity	NPC14030
0.7632	Intermediate Similarity	NPC280778
0.7632	Intermediate Similarity	NPC291957
0.7629	Intermediate Similarity	NPC235575
0.7629	Intermediate Similarity	NPC471181
0.7626	Intermediate Similarity	NPC162694
0.7622	Intermediate Similarity	NPC476434
0.7619	Intermediate Similarity	NPC474770
0.7614	Intermediate Similarity	NPC80956
0.761	Intermediate Similarity	NPC286135
0.7606	Intermediate Similarity	NPC181168
0.7606	Intermediate Similarity	NPC163527
0.7606	Intermediate Similarity	NPC19947
0.7606	Intermediate Similarity	NPC472860
0.7606	Intermediate Similarity	NPC207584
0.7606	Intermediate Similarity	NPC115281
0.7604	Intermediate Similarity	NPC174734
0.7604	Intermediate Similarity	NPC474042
0.7602	Intermediate Similarity	NPC79736
0.7602	Intermediate Similarity	NPC154741
0.7602	Intermediate Similarity	NPC472991
0.7602	Intermediate Similarity	NPC473562
0.7602	Intermediate Similarity	NPC296018
0.7602	Intermediate Similarity	NPC469397
0.7602	Intermediate Similarity	NPC472992
0.7602	Intermediate Similarity	NPC67629
0.76	Intermediate Similarity	NPC475360
0.7594	Intermediate Similarity	NPC476065
0.7594	Intermediate Similarity	NPC238834
0.7592	Intermediate Similarity	NPC470898
0.7592	Intermediate Similarity	NPC469475
0.7592	Intermediate Similarity	NPC469518
0.759	Intermediate Similarity	NPC219600
0.759	Intermediate Similarity	NPC166674
0.759	Intermediate Similarity	NPC477881
0.759	Intermediate Similarity	NPC46640
0.759	Intermediate Similarity	NPC316539
0.759	Intermediate Similarity	NPC472993
0.759	Intermediate Similarity	NPC329816
0.759	Intermediate Similarity	NPC34436
0.759	Intermediate Similarity	NPC263119
0.7586	Intermediate Similarity	NPC83019
0.7581	Intermediate Similarity	NPC65591
0.7581	Intermediate Similarity	NPC245948
0.7581	Intermediate Similarity	NPC474656
0.7581	Intermediate Similarity	NPC178574
0.7579	Intermediate Similarity	NPC288149
0.7577	Intermediate Similarity	NPC207721
0.7577	Intermediate Similarity	NPC180768
0.7577	Intermediate Similarity	NPC204937
0.7577	Intermediate Similarity	NPC181778
0.7577	Intermediate Similarity	NPC149011
0.7576	Intermediate Similarity	NPC8940
0.7565	Intermediate Similarity	NPC229729
0.7565	Intermediate Similarity	NPC477115
0.7565	Intermediate Similarity	NPC231371
0.7565	Intermediate Similarity	NPC473818
0.7565	Intermediate Similarity	NPC298847
0.7565	Intermediate Similarity	NPC185498
0.7563	Intermediate Similarity	NPC267549
0.7563	Intermediate Similarity	NPC476623
0.7563	Intermediate Similarity	NPC476622
0.7563	Intermediate Similarity	NPC476620
0.7563	Intermediate Similarity	NPC477882
0.7563	Intermediate Similarity	NPC476619
0.7563	Intermediate Similarity	NPC477880
0.7563	Intermediate Similarity	NPC476618
0.7563	Intermediate Similarity	NPC476773
0.7563	Intermediate Similarity	NPC476621
0.7561	Intermediate Similarity	NPC476662
0.756	Intermediate Similarity	NPC46990
0.7553	Intermediate Similarity	NPC237946
0.7553	Intermediate Similarity	NPC32373
0.7552	Intermediate Similarity	NPC477884
0.7552	Intermediate Similarity	NPC475738
0.7551	Intermediate Similarity	NPC472607
0.755	Intermediate Similarity	NPC261623
0.755	Intermediate Similarity	NPC111490
0.7539	Intermediate Similarity	NPC249070
0.7539	Intermediate Similarity	NPC33298
0.7539	Intermediate Similarity	NPC90905
0.7539	Intermediate Similarity	NPC4013
0.7539	Intermediate Similarity	NPC285108
0.7538	Intermediate Similarity	NPC35924
0.7538	Intermediate Similarity	NPC178737
0.7538	Intermediate Similarity	NPC38438
0.7538	Intermediate Similarity	NPC254540
0.7538	Intermediate Similarity	NPC205076
0.7538	Intermediate Similarity	NPC67134
0.7538	Intermediate Similarity	NPC211594
0.7538	Intermediate Similarity	NPC172807
0.7538	Intermediate Similarity	NPC48773
0.7538	Intermediate Similarity	NPC47140
0.7538	Intermediate Similarity	NPC199172
0.7538	Intermediate Similarity	NPC307518
0.7537	Intermediate Similarity	NPC204580
0.7527	Intermediate Similarity	NPC267091
0.7526	Intermediate Similarity	NPC285973
0.7526	Intermediate Similarity	NPC96593
0.7526	Intermediate Similarity	NPC289346
0.7526	Intermediate Similarity	NPC24164
0.7526	Intermediate Similarity	NPC53889
0.7526	Intermediate Similarity	NPC225624
0.7526	Intermediate Similarity	NPC239966
0.7526	Intermediate Similarity	NPC203020
0.7525	Intermediate Similarity	NPC198902
0.7514	Intermediate Similarity	NPC24425
0.7513	Intermediate Similarity	NPC156818
0.7513	Intermediate Similarity	NPC475592
0.7513	Intermediate Similarity	NPC254306
0.7513	Intermediate Similarity	NPC114179
0.7513	Intermediate Similarity	NPC160512
0.7513	Intermediate Similarity	NPC233994
0.7513	Intermediate Similarity	NPC211532
0.7513	Intermediate Similarity	NPC68324
0.7513	Intermediate Similarity	NPC289322
0.7513	Intermediate Similarity	NPC38779
0.7512	Intermediate Similarity	NPC476661
0.7512	Intermediate Similarity	NPC252156
0.75	Intermediate Similarity	NPC191306
0.75	Intermediate Similarity	NPC172033
0.75	Intermediate Similarity	NPC473550
0.75	Intermediate Similarity	NPC475865
0.75	Intermediate Similarity	NPC231254
0.75	Intermediate Similarity	NPC215098
0.75	Intermediate Similarity	NPC270335
0.75	Intermediate Similarity	NPC124302
0.75	Intermediate Similarity	NPC46744
0.75	Intermediate Similarity	NPC175230
0.75	Intermediate Similarity	NPC73020
0.75	Intermediate Similarity	NPC14622
0.75	Intermediate Similarity	NPC88560
0.75	Intermediate Similarity	NPC168822
0.75	Intermediate Similarity	NPC163165
0.75	Intermediate Similarity	NPC70290
0.75	Intermediate Similarity	NPC476358

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 NPC475768 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	618
0.2-0.3	1327
0.3-0.4	2312
0.4-0.5	2519
0.5-0.6	1557
0.6-0.7	498
0.7-0.8	112
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
0.8081	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7729	Intermediate Similarity	NPD8151	Discontinued
0.7703	Intermediate Similarity	NPD7827	Phase 1
0.7696	Intermediate Similarity	NPD5006	Approved
0.7696	Intermediate Similarity	NPD5005	Approved
0.766	Intermediate Similarity	NPD6234	Discontinued
0.7656	Intermediate Similarity	NPD3818	Discontinued
0.761	Intermediate Similarity	NPD6823	Phase 2
0.7581	Intermediate Similarity	NPD37	Approved
0.7565	Intermediate Similarity	NPD7228	Approved
0.7563	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD4967	Phase 2
0.7553	Intermediate Similarity	NPD4966	Approved
0.7553	Intermediate Similarity	NPD4965	Approved
0.7524	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD7874	Approved
0.7514	Intermediate Similarity	NPD4005	Discontinued
0.7513	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4420	Approved
0.7488	Intermediate Similarity	NPD7801	Approved
0.7462	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD7007	Discovery
0.7396	Intermediate Similarity	NPD7199	Phase 2
0.7347	Intermediate Similarity	NPD7054	Approved
0.7347	Intermediate Similarity	NPD5844	Phase 1
0.7344	Intermediate Similarity	NPD6746	Phase 2
0.7343	Intermediate Similarity	NPD6781	Approved
0.7343	Intermediate Similarity	NPD6779	Approved
0.7343	Intermediate Similarity	NPD6782	Approved
0.7343	Intermediate Similarity	NPD6778	Approved
0.7343	Intermediate Similarity	NPD6777	Approved
0.7343	Intermediate Similarity	NPD6776	Approved
0.7343	Intermediate Similarity	NPD6780	Approved
0.7324	Intermediate Similarity	NPD7783	Phase 2
0.7324	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD4663	Approved
0.731	Intermediate Similarity	NPD7472	Approved
0.731	Intermediate Similarity	NPD7074	Phase 3
0.7306	Intermediate Similarity	NPD6997	Phase 2
0.7277	Intermediate Similarity	NPD6843	Phase 3
0.7277	Intermediate Similarity	NPD6842	Approved
0.7277	Intermediate Similarity	NPD6841	Approved
0.7273	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD7047	Phase 3
0.7264	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4111	Phase 1
0.7248	Intermediate Similarity	NPD4665	Approved
0.724	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD4002	Approved
0.7238	Intermediate Similarity	NPD4004	Approved
0.7232	Intermediate Similarity	NPD8067	Phase 3
0.7231	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD3450	Approved
0.7225	Intermediate Similarity	NPD2494	Approved
0.7225	Intermediate Similarity	NPD3452	Approved
0.7225	Intermediate Similarity	NPD2493	Approved
0.7222	Intermediate Similarity	NPD7930	Approved
0.7219	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4582	Approved
0.7204	Intermediate Similarity	NPD4583	Approved
0.72	Intermediate Similarity	NPD7549	Discontinued
0.72	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7906	Approved
0.7186	Intermediate Similarity	NPD6797	Phase 2
0.7183	Intermediate Similarity	NPD7701	Phase 2
0.7181	Intermediate Similarity	NPD1653	Approved
0.7173	Intermediate Similarity	NPD1465	Phase 2
0.7164	Intermediate Similarity	NPD4577	Approved
0.7164	Intermediate Similarity	NPD4578	Approved
0.7156	Intermediate Similarity	NPD7696	Phase 3
0.7156	Intermediate Similarity	NPD7697	Approved
0.7156	Intermediate Similarity	NPD7698	Approved
0.715	Intermediate Similarity	NPD7685	Pre-registration
0.715	Intermediate Similarity	NPD7039	Approved
0.715	Intermediate Similarity	NPD7251	Discontinued
0.715	Intermediate Similarity	NPD7038	Approved
0.715	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD5242	Approved
0.7143	Intermediate Similarity	NPD3455	Phase 2
0.7129	Intermediate Similarity	NPD7565	Approved
0.7123	Intermediate Similarity	NPD7870	Phase 2
0.7123	Intermediate Similarity	NPD7871	Phase 2
0.7123	Intermediate Similarity	NPD8320	Phase 1
0.7123	Intermediate Similarity	NPD8319	Approved
0.7114	Intermediate Similarity	NPD7808	Phase 3
0.7107	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6166	Phase 2
0.7107	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7907	Approved
0.7103	Intermediate Similarity	NPD7585	Approved
0.7101	Intermediate Similarity	NPD6534	Approved
0.7101	Intermediate Similarity	NPD3473	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6535	Approved
0.71	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6625	Approved
0.7092	Intermediate Similarity	NPD6232	Discontinued
0.7078	Intermediate Similarity	NPD8404	Phase 2
0.7075	Intermediate Similarity	NPD7435	Discontinued
0.7075	Intermediate Similarity	NPD7497	Discontinued
0.7073	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7473	Discontinued
0.7068	Intermediate Similarity	NPD6385	Approved
0.7068	Intermediate Similarity	NPD6386	Approved
0.7065	Intermediate Similarity	NPD6559	Discontinued
0.7056	Intermediate Similarity	NPD7583	Approved
0.7053	Intermediate Similarity	NPD6212	Phase 3
0.7053	Intermediate Similarity	NPD6213	Phase 3
0.7053	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2488	Approved
0.7039	Intermediate Similarity	NPD2490	Approved
0.7033	Intermediate Similarity	NPD2974	Approved
0.7033	Intermediate Similarity	NPD2975	Approved
0.7033	Intermediate Similarity	NPD2973	Approved
0.7031	Intermediate Similarity	NPD1934	Approved
0.7022	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD8059	Phase 3
0.7016	Intermediate Similarity	NPD4380	Phase 2
0.7014	Intermediate Similarity	NPD4580	Approved
0.7009	Intermediate Similarity	NPD7999	Approved
0.7005	Intermediate Similarity	NPD7296	Approved
0.7	Intermediate Similarity	NPD7699	Phase 2
0.7	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7700	Phase 2
0.6995	Remote Similarity	NPD2978	Approved
0.6995	Remote Similarity	NPD2801	Approved
0.6995	Remote Similarity	NPD2977	Approved
0.6989	Remote Similarity	NPD3750	Approved
0.6977	Remote Similarity	NPD7584	Approved
0.6976	Remote Similarity	NPD8150	Discontinued
0.6968	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3817	Phase 2
0.6959	Remote Similarity	NPD5402	Approved
0.6957	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2491	Approved
0.6948	Remote Similarity	NPD3057	Approved
0.6948	Remote Similarity	NPD3448	Approved
0.6943	Remote Similarity	NPD6723	Discontinued
0.6935	Remote Similarity	NPD2489	Approved
0.6935	Remote Similarity	NPD27	Approved
0.6934	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD3823	Discontinued
0.6923	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3882	Suspended
0.6919	Remote Similarity	NPD3051	Approved
0.6912	Remote Similarity	NPD8313	Approved
0.6912	Remote Similarity	NPD8312	Approved
0.6908	Remote Similarity	NPD8361	Approved
0.6908	Remote Similarity	NPD8360	Approved
0.6907	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD5494	Approved
0.6893	Remote Similarity	NPD5038	Approved
0.6893	Remote Similarity	NPD5037	Approved
0.6891	Remote Similarity	NPD5089	Approved
0.6891	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD5090	Approved
0.6888	Remote Similarity	NPD4055	Discovery
0.6884	Remote Similarity	NPD2969	Approved
0.6884	Remote Similarity	NPD2970	Approved
0.6878	Remote Similarity	NPD8054	Approved
0.6878	Remote Similarity	NPD8053	Approved
0.6878	Remote Similarity	NPD4357	Discontinued
0.6875	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5353	Approved
0.6869	Remote Similarity	NPD2972	Approved
0.6869	Remote Similarity	NPD3533	Approved
0.686	Remote Similarity	NPD7291	Discontinued
0.686	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4107	Approved
0.685	Remote Similarity	NPD4481	Phase 3
0.6849	Remote Similarity	NPD8367	Approved
0.6849	Remote Similarity	NPD8153	Approved
0.6849	Remote Similarity	NPD8152	Approved
0.6845	Remote Similarity	NPD5036	Approved
0.6837	Remote Similarity	NPD7680	Approved
0.6834	Remote Similarity	NPD7315	Approved
0.6832	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7310	Approved
0.6829	Remote Similarity	NPD7311	Approved
0.6829	Remote Similarity	NPD7313	Approved
0.6829	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7312	Approved
0.6827	Remote Similarity	NPD8435	Approved
0.6827	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4361	Phase 2
0.6825	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8461	Discontinued
0.6806	Remote Similarity	NPD4040	Phase 1
0.6805	Remote Similarity	NPD8492	Approved
0.6803	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD8407	Phase 2
0.6796	Remote Similarity	NPD7309	Approved
0.6792	Remote Similarity	NPD8485	Approved
0.6789	Remote Similarity	NPD1511	Approved
0.6786	Remote Similarity	NPD2899	Discontinued
0.678	Remote Similarity	NPD4955	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