NPASS Compound

Structure

NPC171706 OpenBabel07101719122D 44 48 0 0 1 0 0 0 0 0999 V2000 2.3164 -1.2784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0292 -2.4373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2946 -1.0705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 -1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6765 -2.9726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7926 1.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6557 2.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0074 -2.2294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9266 1.8838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2435 1.5748 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9637 -1.8136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6547 -2.7647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7926 0.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2435 3.1928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6180 -1.9021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0605 1.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1945 1.8838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9266 -0.1162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 1.6942 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0605 0.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3383 1.4863 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6473 0.5352 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1945 2.8838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9344 0.6237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9266 2.8838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9418 -1.6057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3238 -3.5078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6586 -0.1162 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9344 4.1439 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 -2.8532 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9266 -1.1162 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0511 2.6453 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1945 -0.1162 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0074 2.2294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6254 0.3273 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6036 -0.1194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7926 3.3838 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9563 0.4158 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 -1.2872 -1.1590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0605 3.3838 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 9 1 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 12 1 0 0 0 0 4 17 1 0 0 0 0 5 9 2 0 0 0 0 5 13 1 0 0 0 0 6 10 2 0 0 0 0 6 14 1 0 0 0 0 7 11 1 0 0 0 0 7 15 1 0 0 0 0 8 41 1 0 0 0 0 10 18 1 0 0 0 0 10 27 1 0 0 0 0 11 19 1 0 0 0 0 11 26 1 1 0 0 0 12 13 2 0 0 0 0 12 29 1 0 0 0 0 13 30 1 0 0 0 0 14 20 2 0 0 0 0 14 31 1 0 0 0 0 15 25 1 0 0 0 0 15 32 2 0 0 0 0 16 8 1 1 0 0 0 16 21 1 0 0 0 0 16 42 1 0 0 0 0 17 33 2 0 0 0 0 17 43 1 0 0 0 0 18 19 1 0 0 0 0 18 22 2 0 0 0 0 19 25 2 0 0 0 0 20 22 1 0 0 0 0 20 34 1 0 0 0 0 21 23 1 0 0 0 0 21 35 1 6 0 0 0 22 36 1 0 0 0 0 23 24 1 0 0 0 0 23 37 1 1 0 0 0 24 28 1 0 0 0 0 24 38 1 6 0 0 0 25 44 1 0 0 0 0 26 39 2 0 0 0 0 26 41 1 0 0 0 0 27 40 2 0 0 0 0 27 44 1 0 0 0 0 28 42 1 0 0 0 0 28 43 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	616.11
Volume:	559.068
LogP:	1.102
LogD:	0.269
LogS:	-4.765
# Rotatable Bonds:	7
TPSA:	277.27
# H-Bond Aceptor:	16
# H-Bond Donor:	10
# Rings:	5
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.075
Synthetic Accessibility Score:	4.944
Fsp3:	0.214
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.342
MDCK Permeability:	2.43872946157353e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.205
20% Bioavailability (F20%):	0.279
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	90.49224090576172%
Volume Distribution (VD):	0.641
Pgp-substrate:	17.807931900024414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.317
CYP1A2-substrate:	0.016
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.035
CYP2C9-inhibitor:	0.276
CYP2C9-substrate:	0.062
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.003

ADMET: Excretion

Clearance (CL):	1.784
Half-life (T1/2):	0.847

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.204
Drug-inuced Liver Injury (DILI):	0.993
AMES Toxicity:	0.595
Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.832
Carcinogencity:	0.148
Eye Corrosion:	0.003
Eye Irritation:	0.221
Respiratory Toxicity:	0.032

Download Data

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

Natural Product: NPC171706

Natural Product ID:	NPC171706
*Common Name:**	Balanophotannin D
IUPAC Name:	[(2R,3S,4S,5R,6S)-6-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (1S)-7,8,9-trihydroxy-3,5-dioxo-1,2-dihydrocyclopenta[c]isochromene-1-carboxylate
Synonyms:	balanophotannin D
Standard InCHIKey:	URJGURKNABRVCH-ATYMIDRYSA-N
Standard InCHI:	InChI=1S/C28H24O16/c29-12-3-1-9(5-13(12)30)2-4-17(33)43-28-24(38)23(37)21(35)16(42-28)8-41-26(39)11-7-15(32)25-19(11)18-10(27(40)44-25)6-14(31)20(34)22(18)36/h1-6,11,16,21,23-24,28-31,34-38H,7-8H2/b4-2+/t11-,16+,21+,23-,24+,28-/m0/s1
SMILES:	O=C(O[C@@H]1O[C@H](COC(=O)[C@H]2CC(=O)c3c2c2c(O)c(O)c(cc2c(=O)o3)O)[C@H]([C@@H]([C@H]1O)O)O)/C=C/c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506571
PubChem CID:	24862008
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0003003] Hydroxycinnamic acid 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
NPO15233	Balanophora japonica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18302336]
NPO15233	Balanophora japonica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15233	Balanophora japonica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15233	Balanophora japonica	Species	Balanophoraceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	17410.0	nM	PMID[525215]

☑ 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 NPC171706 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	455
0.1-0.2	1793
0.2-0.3	3715
0.3-0.4	8816
0.4-0.5	9460
0.5-0.6	4732
0.6-0.7	5930
0.7-0.8	6260
0.8-0.85	1095
0.85-0.9	422
0.9-0.95	17
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9699	High Similarity	NPC198902
0.9091	High Similarity	NPC14030
0.9091	High Similarity	NPC291957
0.907	High Similarity	NPC170203
0.9036	High Similarity	NPC470898
0.9006	High Similarity	NPC473713
0.8971	High Similarity	NPC475360
0.8896	High Similarity	NPC125487
0.8896	High Similarity	NPC281703
0.8882	High Similarity	NPC155763
0.8882	High Similarity	NPC20505
0.8882	High Similarity	NPC235260
0.8876	High Similarity	NPC470271
0.8876	High Similarity	NPC311389
0.8848	High Similarity	NPC135222
0.8848	High Similarity	NPC474010
0.8844	High Similarity	NPC253521
0.8844	High Similarity	NPC37668
0.8844	High Similarity	NPC113836
0.8837	High Similarity	NPC253685
0.8834	High Similarity	NPC161159
0.883	High Similarity	NPC175107
0.883	High Similarity	NPC190003
0.8827	High Similarity	NPC140151
0.8824	High Similarity	NPC138927
0.8817	High Similarity	NPC175793
0.8786	High Similarity	NPC61904
0.8786	High Similarity	NPC144097
0.8786	High Similarity	NPC296018
0.8786	High Similarity	NPC154741
0.8779	High Similarity	NPC4390
0.8773	High Similarity	NPC92747
0.8773	High Similarity	NPC265862
0.8772	High Similarity	NPC116864
0.8772	High Similarity	NPC244776
0.8772	High Similarity	NPC470272
0.8765	High Similarity	NPC43918
0.8765	High Similarity	NPC261411
0.8765	High Similarity	NPC9099
0.8765	High Similarity	NPC190204
0.8736	High Similarity	NPC267680
0.8736	High Similarity	NPC217387
0.8736	High Similarity	NPC293626
0.8736	High Similarity	NPC35167
0.8736	High Similarity	NPC476773
0.8736	High Similarity	NPC196127
0.8736	High Similarity	NPC258044
0.8735	High Similarity	NPC187205
0.8735	High Similarity	NPC49173
0.8728	High Similarity	NPC34267
0.8728	High Similarity	NPC223426
0.8728	High Similarity	NPC81042
0.8728	High Similarity	NPC115760
0.8728	High Similarity	NPC135277
0.8728	High Similarity	NPC214621
0.8728	High Similarity	NPC210094
0.8728	High Similarity	NPC101191
0.8728	High Similarity	NPC43211
0.8728	High Similarity	NPC49344
0.8728	High Similarity	NPC237435
0.8721	High Similarity	NPC153755
0.872	High Similarity	NPC61152
0.872	High Similarity	NPC16024
0.872	High Similarity	NPC3746
0.872	High Similarity	NPC205037
0.872	High Similarity	NPC44260
0.8708	High Similarity	NPC7839
0.8708	High Similarity	NPC173872
0.8708	High Similarity	NPC142291
0.8708	High Similarity	NPC119094
0.8706	High Similarity	NPC145038
0.8706	High Similarity	NPC281131
0.8706	High Similarity	NPC56077
0.8706	High Similarity	NPC253662
0.8706	High Similarity	NPC274618
0.8706	High Similarity	NPC118284
0.8706	High Similarity	NPC276222
0.8706	High Similarity	NPC88789
0.8706	High Similarity	NPC308404
0.8706	High Similarity	NPC179950
0.8704	High Similarity	NPC92117
0.8693	High Similarity	NPC135831
0.8693	High Similarity	NPC297503
0.8693	High Similarity	NPC97119
0.8678	High Similarity	NPC211532
0.8678	High Similarity	NPC471669
0.8678	High Similarity	NPC297574
0.8678	High Similarity	NPC472385
0.8678	High Similarity	NPC233994
0.8678	High Similarity	NPC198324
0.8678	High Similarity	NPC472723
0.8678	High Similarity	NPC89127
0.8678	High Similarity	NPC268533
0.8663	High Similarity	NPC136042
0.8663	High Similarity	NPC29958
0.8663	High Similarity	NPC47521
0.8663	High Similarity	NPC72249
0.8663	High Similarity	NPC67326
0.8663	High Similarity	NPC156869
0.8663	High Similarity	NPC259896
0.8663	High Similarity	NPC255157
0.8663	High Similarity	NPC254855
0.8663	High Similarity	NPC206123
0.8659	High Similarity	NPC201814
0.8655	High Similarity	NPC223424
0.8655	High Similarity	NPC84362
0.8655	High Similarity	NPC317489
0.8655	High Similarity	NPC149244
0.8655	High Similarity	NPC173637
0.8655	High Similarity	NPC48640
0.8655	High Similarity	NPC31034
0.8655	High Similarity	NPC92565
0.8655	High Similarity	NPC127546
0.8655	High Similarity	NPC160156
0.8655	High Similarity	NPC52550
0.8647	High Similarity	NPC19388
0.8647	High Similarity	NPC240431
0.8647	High Similarity	NPC55786
0.8647	High Similarity	NPC277205
0.8644	High Similarity	NPC231254
0.8642	High Similarity	NPC120621
0.8642	High Similarity	NPC248257
0.8639	High Similarity	NPC145847
0.8636	High Similarity	NPC208797
0.8636	High Similarity	NPC53680
0.8631	High Similarity	NPC24627
0.8629	High Similarity	NPC173837
0.8629	High Similarity	NPC469418
0.8629	High Similarity	NPC139571
0.8629	High Similarity	NPC217520
0.8623	High Similarity	NPC472860
0.8621	High Similarity	NPC264735
0.8621	High Similarity	NPC477848
0.8614	High Similarity	NPC203757
0.8613	High Similarity	NPC33054
0.8613	High Similarity	NPC203259
0.8613	High Similarity	NPC471748
0.8613	High Similarity	NPC60735
0.8613	High Similarity	NPC176740
0.8613	High Similarity	NPC26230
0.8613	High Similarity	NPC245452
0.8613	High Similarity	NPC471725
0.8613	High Similarity	NPC155877
0.8613	High Similarity	NPC134532
0.8605	High Similarity	NPC120099
0.8605	High Similarity	NPC270578
0.8605	High Similarity	NPC203050
0.8605	High Similarity	NPC225434
0.8605	High Similarity	NPC328321
0.8605	High Similarity	NPC52382
0.8605	High Similarity	NPC219904
0.8605	High Similarity	NPC223747
0.8596	High Similarity	NPC255615
0.8596	High Similarity	NPC21100
0.8596	High Similarity	NPC197285
0.8596	High Similarity	NPC113968
0.8596	High Similarity	NPC328940
0.8596	High Similarity	NPC277174
0.8596	High Similarity	NPC135599
0.8596	High Similarity	NPC73855
0.8596	High Similarity	NPC67037
0.8588	High Similarity	NPC36138
0.8588	High Similarity	NPC470718
0.8588	High Similarity	NPC156785
0.8588	High Similarity	NPC470449
0.8588	High Similarity	NPC470446
0.8588	High Similarity	NPC241781
0.8588	High Similarity	NPC470445
0.8588	High Similarity	NPC107987
0.8588	High Similarity	NPC109990
0.8588	High Similarity	NPC168822
0.8588	High Similarity	NPC470447
0.8588	High Similarity	NPC162394
0.858	High Similarity	NPC80956
0.858	High Similarity	NPC195114
0.8571	High Similarity	NPC472380
0.8571	High Similarity	NPC470949
0.8571	High Similarity	NPC8573
0.8571	High Similarity	NPC472384
0.8571	High Similarity	NPC472382
0.8571	High Similarity	NPC65563
0.8571	High Similarity	NPC473862
0.8563	High Similarity	NPC169977
0.8563	High Similarity	NPC42773
0.8563	High Similarity	NPC473550
0.8563	High Similarity	NPC46640
0.8563	High Similarity	NPC45522
0.8563	High Similarity	NPC21666
0.8563	High Similarity	NPC24043
0.8563	High Similarity	NPC219600
0.8563	High Similarity	NPC34436
0.8563	High Similarity	NPC166674
0.8563	High Similarity	NPC101026
0.8563	High Similarity	NPC263119
0.8555	High Similarity	NPC181778
0.8555	High Similarity	NPC95866
0.8555	High Similarity	NPC285197
0.8555	High Similarity	NPC149011
0.8555	High Similarity	NPC245014
0.8555	High Similarity	NPC84265

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 NPC171706 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	386
0.1-0.2	947
0.2-0.3	1979
0.3-0.4	2667
0.4-0.5	1869
0.5-0.6	859
0.6-0.7	302
0.7-0.8	116
0.8-0.85	22
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8728	High Similarity	NPD4338	Clinical (unspecified phase)
0.8613	High Similarity	NPD6797	Phase 2
0.8563	High Similarity	NPD7251	Discontinued
0.8547	High Similarity	NPD3818	Discontinued
0.8409	Intermediate Similarity	NPD7808	Phase 3
0.8343	Intermediate Similarity	NPD7472	Approved
0.8343	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8295	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD7054	Approved
0.8239	Intermediate Similarity	NPD7074	Phase 3
0.8167	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD7685	Pre-registration
0.8142	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7228	Approved
0.8079	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD6234	Discontinued
0.8012	Intermediate Similarity	NPD1465	Phase 2
0.8011	Intermediate Similarity	NPD6166	Phase 2
0.8011	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6190	Approved
0.7965	Intermediate Similarity	NPD3817	Phase 2
0.7953	Intermediate Similarity	NPD37	Approved
0.7943	Intermediate Similarity	NPD7199	Phase 2
0.7941	Intermediate Similarity	NPD4380	Phase 2
0.7919	Intermediate Similarity	NPD4967	Phase 2
0.7919	Intermediate Similarity	NPD3882	Suspended
0.7919	Intermediate Similarity	NPD4966	Approved
0.7919	Intermediate Similarity	NPD4965	Approved
0.7877	Intermediate Similarity	NPD5844	Phase 1
0.7874	Intermediate Similarity	NPD7075	Discontinued
0.7865	Intermediate Similarity	NPD7473	Discontinued
0.7861	Intermediate Similarity	NPD5402	Approved
0.7849	Intermediate Similarity	NPD1934	Approved
0.7821	Intermediate Similarity	NPD3751	Discontinued
0.7803	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD6232	Discontinued
0.7765	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD8313	Approved
0.776	Intermediate Similarity	NPD8312	Approved
0.7758	Intermediate Similarity	NPD7266	Discontinued
0.7747	Intermediate Similarity	NPD7240	Approved
0.7747	Intermediate Similarity	NPD6559	Discontinued
0.7746	Intermediate Similarity	NPD6801	Discontinued
0.772	Intermediate Similarity	NPD7435	Discontinued
0.7719	Intermediate Similarity	NPD1653	Approved
0.7706	Intermediate Similarity	NPD1512	Approved
0.7701	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD2801	Approved
0.768	Intermediate Similarity	NPD8320	Phase 1
0.768	Intermediate Similarity	NPD8319	Approved
0.7669	Intermediate Similarity	NPD230	Phase 1
0.7661	Intermediate Similarity	NPD5403	Approved
0.7619	Intermediate Similarity	NPD3750	Approved
0.7614	Intermediate Similarity	NPD8151	Discontinued
0.76	Intermediate Similarity	NPD7819	Suspended
0.7598	Intermediate Similarity	NPD3787	Discontinued
0.7588	Intermediate Similarity	NPD1511	Approved
0.7584	Intermediate Similarity	NPD5494	Approved
0.7579	Intermediate Similarity	NPD6535	Approved
0.7579	Intermediate Similarity	NPD6534	Approved
0.7565	Intermediate Similarity	NPD6782	Approved
0.7565	Intermediate Similarity	NPD6776	Approved
0.7565	Intermediate Similarity	NPD6778	Approved
0.7565	Intermediate Similarity	NPD6777	Approved
0.7565	Intermediate Similarity	NPD6781	Approved
0.7565	Intermediate Similarity	NPD6780	Approved
0.7565	Intermediate Similarity	NPD6779	Approved
0.7553	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5401	Approved
0.754	Intermediate Similarity	NPD8150	Discontinued
0.7487	Intermediate Similarity	NPD7874	Approved
0.7487	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6799	Approved
0.7461	Intermediate Similarity	NPD7700	Phase 2
0.7461	Intermediate Similarity	NPD7699	Phase 2
0.7429	Intermediate Similarity	NPD6599	Discontinued
0.7425	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD943	Approved
0.7384	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD3749	Approved
0.736	Intermediate Similarity	NPD7697	Approved
0.736	Intermediate Similarity	NPD7696	Phase 3
0.736	Intermediate Similarity	NPD7698	Approved
0.7354	Intermediate Similarity	NPD8434	Phase 2
0.7341	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7870	Phase 2
0.7323	Intermediate Similarity	NPD7871	Phase 2
0.7321	Intermediate Similarity	NPD1510	Phase 2
0.7321	Intermediate Similarity	NPD3748	Approved
0.731	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD8455	Phase 2
0.73	Intermediate Similarity	NPD7701	Phase 2
0.7294	Intermediate Similarity	NPD1549	Phase 2
0.7288	Intermediate Similarity	NPD7411	Suspended
0.7277	Intermediate Similarity	NPD7801	Approved
0.7273	Intermediate Similarity	NPD7680	Approved
0.7263	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6959	Discontinued
0.7241	Intermediate Similarity	NPD2532	Approved
0.7241	Intermediate Similarity	NPD2533	Approved
0.7241	Intermediate Similarity	NPD2534	Approved
0.7238	Intermediate Similarity	NPD919	Approved
0.7235	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4628	Phase 3
0.7186	Intermediate Similarity	NPD1613	Approved
0.7186	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7458	Discontinued
0.7174	Intermediate Similarity	NPD3926	Phase 2
0.7169	Intermediate Similarity	NPD3764	Approved
0.7165	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD6212	Phase 3
0.7165	Intermediate Similarity	NPD6213	Phase 3
0.7143	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD9269	Phase 2
0.7079	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD2796	Approved
0.7068	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD1247	Approved
0.7062	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7799	Discontinued
0.705	Intermediate Similarity	NPD6823	Phase 2
0.7045	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7783	Phase 2
0.7024	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD8166	Discontinued
0.7006	Intermediate Similarity	NPD3027	Phase 3
0.7005	Intermediate Similarity	NPD7930	Approved
0.6983	Remote Similarity	NPD3226	Approved
0.6982	Remote Similarity	NPD1240	Approved
0.6973	Remote Similarity	NPD8127	Discontinued
0.697	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7585	Approved
0.6954	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6355	Discontinued
0.694	Remote Similarity	NPD7768	Phase 2
0.6912	Remote Similarity	NPD7583	Approved
0.6912	Remote Similarity	NPD7584	Approved
0.6911	Remote Similarity	NPD8368	Discontinued
0.691	Remote Similarity	NPD6273	Approved
0.6901	Remote Similarity	NPD1607	Approved
0.6898	Remote Similarity	NPD5242	Approved
0.6893	Remote Similarity	NPD7390	Discontinued
0.6891	Remote Similarity	NPD8407	Phase 2
0.6886	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5353	Approved
0.6882	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4060	Phase 1
0.6879	Remote Similarity	NPD2935	Discontinued
0.6864	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6674	Discontinued
0.6852	Remote Similarity	NPD9268	Approved
0.6845	Remote Similarity	NPD5710	Approved
0.6845	Remote Similarity	NPD5711	Approved
0.6845	Remote Similarity	NPD7229	Phase 3
0.6842	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD7236	Approved
0.6818	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD5006	Approved
0.6798	Remote Similarity	NPD5005	Approved
0.6793	Remote Similarity	NPD4288	Approved
0.6782	Remote Similarity	NPD5406	Approved
0.6782	Remote Similarity	NPD1551	Phase 2
0.6782	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5408	Approved
0.6782	Remote Similarity	NPD5405	Approved
0.6782	Remote Similarity	NPD5404	Approved
0.6782	Remote Similarity	NPD6099	Approved
0.6782	Remote Similarity	NPD6100	Approved
0.6778	Remote Similarity	NPD920	Approved
0.6771	Remote Similarity	NPD5953	Discontinued
0.6765	Remote Similarity	NPD6798	Discontinued
0.6763	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.676	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD1933	Approved
0.6743	Remote Similarity	NPD2346	Discontinued
0.6743	Remote Similarity	NPD5762	Approved
0.6743	Remote Similarity	NPD5763	Approved
0.674	Remote Similarity	NPD7239	Suspended
0.6703	Remote Similarity	NPD3455	Phase 2
0.6699	Remote Similarity	NPD7999	Approved
0.6687	Remote Similarity	NPD9545	Approved
0.6686	Remote Similarity	NPD9494	Approved
0.6684	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4004	Approved
0.6683	Remote Similarity	NPD4420	Approved
0.6683	Remote Similarity	NPD4002	Approved
0.6667	Remote Similarity	NPD8361	Approved
0.6667	Remote Similarity	NPD3452	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