NPASS Compound

Structure

NPC469664 OpenBabel07101718222D 44 49 0 0 1 0 0 0 0 0999 V2000 -0.0000 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 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 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 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 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 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 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 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 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 12 1 0 0 0 0 3 11 1 0 0 0 0 3 13 1 0 0 0 0 4 12 1 0 0 0 0 4 14 1 0 0 0 0 5 13 2 0 0 0 0 5 17 1 0 0 0 0 6 14 2 0 0 0 0 6 18 1 0 0 0 0 7 15 2 0 0 0 0 7 23 1 0 0 0 0 8 16 2 0 0 0 0 8 24 1 0 0 0 0 9 19 1 0 0 0 0 9 21 2 0 0 0 0 10 20 1 0 0 0 0 10 22 2 0 0 0 0 11 33 1 0 0 0 0 12 34 2 0 0 0 0 13 43 1 0 0 0 0 14 44 1 0 0 0 0 15 25 1 0 0 0 0 15 27 1 0 0 0 0 16 26 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 17 35 2 0 0 0 0 18 30 1 0 0 0 0 18 36 2 0 0 0 0 19 25 2 0 0 0 0 19 37 1 0 0 0 0 20 26 2 0 0 0 0 20 38 1 0 0 0 0 21 27 1 0 0 0 0 21 39 1 0 0 0 0 22 28 1 0 0 0 0 22 40 1 0 0 0 0 23 29 2 0 0 0 0 23 43 1 0 0 0 0 24 30 2 0 0 0 0 24 44 1 0 0 0 0 25 26 1 0 0 0 0 27 31 2 0 0 0 0 28 32 2 0 0 0 0 29 31 1 0 0 0 0 30 32 1 0 0 0 0 31 41 1 0 0 0 0 32 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	600.13
Volume:	576.625
LogP:	4.904
LogD:	1.694
LogS:	-4.651
# Rotatable Bonds:	5
TPSA:	219.1
# H-Bond Aceptor:	12
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.139
Synthetic Accessibility Score:	4.13
Fsp3:	0.156
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.867
MDCK Permeability:	4.562537014862755e-06
Pgp-inhibitor:	0.04
Pgp-substrate:	0.938
Human Intestinal Absorption (HIA):	0.983
20% Bioavailability (F20%):	0.565
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	84.00262451171875%
Volume Distribution (VD):	0.532
Pgp-substrate:	35.88127136230469%

ADMET: Metabolism

CYP1A2-inhibitor:	0.537
CYP1A2-substrate:	0.468
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.79
CYP2C9-substrate:	0.79
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.185
CYP3A4-inhibitor:	0.043
CYP3A4-substrate:	0.062

ADMET: Excretion

Clearance (CL):	1.777
Half-life (T1/2):	0.362

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.226
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.169
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.821
Carcinogencity:	0.01
Eye Corrosion:	0.003
Eye Irritation:	0.811
Respiratory Toxicity:	0.02

Download Data

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

Natural Product: NPC469664

Natural Product ID:	NPC469664
*Common Name:**	Hypochromin A
IUPAC Name:	5,6,8-trihydroxy-2-(2-hydroxypropyl)-9-[5,6,8-trihydroxy-4-oxo-2-(2-oxopropyl)benzo[g]chromen-9-yl]benzo[g]chromen-4-one
Synonyms:
Standard InCHIKey:	DELYIJJKVUTVRM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C32H24O12/c1-11(33)3-13-5-17(35)29-23(43-13)7-15-25(19(37)9-21(39)27(15)31(29)41)26-16-8-24-30(18(36)6-14(44-24)4-12(2)34)32(42)28(16)22(40)10-20(26)38/h5-11,33,37-42H,3-4H2,1-2H3
SMILES:	CC(Cc1cc(=O)c2c(o1)cc1c(c2O)c(O)cc(c1c1c(O)cc(c2c1cc1oc(CC(=O)C)cc(=O)c1c2O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097203
PubChem CID:	46210036
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

*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
NPO32888	hypocrea vinosa	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20192239]

☑ 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	3
Others	6

Activity Type	# Activity
Cell Line	5
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	50000.0	nM	PMID[511216]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	870.0	nM	PMID[511216]
NPT737	Cell Line	HUVEC	Homo sapiens	Inhibition	=	100.0	%	PMID[511216]
NPT737	Cell Line	HUVEC	Homo sapiens	Inhibition	=	62.2	%	PMID[511216]
NPT737	Cell Line	HUVEC	Homo sapiens	Inhibition	=	28.9	%	PMID[511216]
NPT2	Others	Unspecified		Inhibition	=	73.4	%	PMID[511216]
NPT2	Others	Unspecified		Inhibition	=	21.9	%	PMID[511216]
NPT2	Others	Unspecified		Inhibition	=	0.0	%	PMID[511216]
NPT2	Others	Unspecified		IC50	=	58700.0	nM	PMID[511216]

☑ 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 NPC469664 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	442
0.1-0.2	1840
0.2-0.3	3743
0.3-0.4	10045
0.4-0.5	8930
0.5-0.6	4038
0.6-0.7	5442
0.7-0.8	4987
0.8-0.85	2580
0.85-0.9	589
0.9-0.95	55
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9806	High Similarity	NPC189552
0.9806	High Similarity	NPC273467
0.9742	High Similarity	NPC186325
0.9742	High Similarity	NPC312993
0.9677	High Similarity	NPC177650
0.9551	High Similarity	NPC55443
0.9551	High Similarity	NPC18699
0.9494	High Similarity	NPC15374
0.9359	High Similarity	NPC121649
0.9359	High Similarity	NPC248739
0.9359	High Similarity	NPC150908
0.9359	High Similarity	NPC205026
0.9359	High Similarity	NPC158027
0.9359	High Similarity	NPC254351
0.9359	High Similarity	NPC186227
0.9359	High Similarity	NPC52611
0.9359	High Similarity	NPC14606
0.9359	High Similarity	NPC265624
0.9359	High Similarity	NPC159707
0.9359	High Similarity	NPC100049
0.9359	High Similarity	NPC215203
0.9308	High Similarity	NPC18380
0.9304	High Similarity	NPC51760
0.9295	High Similarity	NPC303485
0.9295	High Similarity	NPC71061
0.9295	High Similarity	NPC72425
0.9295	High Similarity	NPC194593
0.9295	High Similarity	NPC290830
0.9245	High Similarity	NPC292863
0.9245	High Similarity	NPC470342
0.9245	High Similarity	NPC472060
0.9245	High Similarity	NPC184326
0.9245	High Similarity	NPC472052
0.9236	High Similarity	NPC66441
0.9236	High Similarity	NPC182555
0.9193	High Similarity	NPC290160
0.9187	High Similarity	NPC137232
0.9187	High Similarity	NPC312273
0.9187	High Similarity	NPC472261
0.9187	High Similarity	NPC301256
0.9182	High Similarity	NPC195167
0.9182	High Similarity	NPC324736
0.9172	High Similarity	NPC329844
0.9167	High Similarity	NPC149526
0.9167	High Similarity	NPC111112
0.9167	High Similarity	NPC138299
0.9167	High Similarity	NPC474417
0.9167	High Similarity	NPC222713
0.9167	High Similarity	NPC232645
0.9167	High Similarity	NPC72958
0.9167	High Similarity	NPC67322
0.9161	High Similarity	NPC158338
0.9161	High Similarity	NPC100985
0.9161	High Similarity	NPC97028
0.9161	High Similarity	NPC65589
0.9161	High Similarity	NPC97029
0.9161	High Similarity	NPC288036
0.9157	High Similarity	NPC216307
0.9141	High Similarity	NPC324522
0.9141	High Similarity	NPC105414
0.9141	High Similarity	NPC470341
0.9141	High Similarity	NPC472058
0.9141	High Similarity	NPC234497
0.913	High Similarity	NPC473012
0.9119	High Similarity	NPC475184
0.9119	High Similarity	NPC257166
0.9114	High Similarity	NPC300668
0.9114	High Similarity	NPC134171
0.9108	High Similarity	NPC87708
0.9097	High Similarity	NPC256672
0.9097	High Similarity	NPC27221
0.9097	High Similarity	NPC7025
0.9091	High Similarity	NPC477836
0.908	High Similarity	NPC251336
0.908	High Similarity	NPC30027
0.908	High Similarity	NPC477835
0.9074	High Similarity	NPC473009
0.9062	High Similarity	NPC105584
0.9062	High Similarity	NPC51247
0.9062	High Similarity	NPC15815
0.9057	High Similarity	NPC32867
0.9051	High Similarity	NPC210942
0.9051	High Similarity	NPC169990
0.9045	High Similarity	NPC478148
0.9032	High Similarity	NPC7943
0.9032	High Similarity	NPC123202
0.9032	High Similarity	NPC22005
0.9018	High Similarity	NPC473010
0.9006	High Similarity	NPC121647
0.9006	High Similarity	NPC195136
0.9	High Similarity	NPC1796
0.8994	High Similarity	NPC226656
0.8994	High Similarity	NPC66508
0.8987	High Similarity	NPC154683
0.8987	High Similarity	NPC40356
0.8987	High Similarity	NPC174086
0.8982	High Similarity	NPC477991
0.8982	High Similarity	NPC477992
0.8981	High Similarity	NPC202595
0.897	High Similarity	NPC300307
0.897	High Similarity	NPC259905
0.897	High Similarity	NPC475212
0.8963	High Similarity	NPC272502
0.8944	High Similarity	NPC295090
0.8944	High Similarity	NPC472617
0.8941	High Similarity	NPC473631
0.8941	High Similarity	NPC293227
0.8941	High Similarity	NPC475662
0.8941	High Similarity	NPC473717
0.8938	High Similarity	NPC146211
0.8938	High Similarity	NPC56049
0.8938	High Similarity	NPC54830
0.8938	High Similarity	NPC69531
0.8935	High Similarity	NPC153578
0.8935	High Similarity	NPC299149
0.8935	High Similarity	NPC277710
0.8935	High Similarity	NPC114257
0.8931	High Similarity	NPC193200
0.8931	High Similarity	NPC324447
0.8931	High Similarity	NPC121568
0.8924	High Similarity	NPC470569
0.8922	High Similarity	NPC213052
0.8917	High Similarity	NPC291746
0.8917	High Similarity	NPC288840
0.8917	High Similarity	NPC477221
0.8917	High Similarity	NPC5173
0.8917	High Similarity	NPC3642
0.891	High Similarity	NPC34802
0.891	High Similarity	NPC290194
0.8909	High Similarity	NPC253730
0.8909	High Similarity	NPC76647
0.8909	High Similarity	NPC286230
0.8903	High Similarity	NPC224714
0.8902	High Similarity	NPC169471
0.8896	High Similarity	NPC473011
0.8889	High Similarity	NPC42965
0.8889	High Similarity	NPC226462
0.8889	High Similarity	NPC98023
0.8889	High Similarity	NPC470810
0.8882	High Similarity	NPC271741
0.8882	High Similarity	NPC281137
0.8882	High Similarity	NPC208258
0.8882	High Similarity	NPC287789
0.8882	High Similarity	NPC282390
0.8875	High Similarity	NPC79375
0.8875	High Similarity	NPC37253
0.8869	High Similarity	NPC300657
0.8868	High Similarity	NPC43345
0.8868	High Similarity	NPC39154
0.8868	High Similarity	NPC115601
0.8868	High Similarity	NPC273483
0.8868	High Similarity	NPC78324
0.8868	High Similarity	NPC208011
0.8862	High Similarity	NPC4200
0.8861	High Similarity	NPC472633
0.8861	High Similarity	NPC37348
0.8861	High Similarity	NPC147735
0.8861	High Similarity	NPC470568
0.8855	High Similarity	NPC188079
0.8854	High Similarity	NPC106328
0.8854	High Similarity	NPC35150
0.8854	High Similarity	NPC122894
0.8848	High Similarity	NPC320741
0.8848	High Similarity	NPC178173
0.8848	High Similarity	NPC178851
0.8848	High Similarity	NPC171985
0.8846	High Similarity	NPC290133
0.8846	High Similarity	NPC24136
0.8846	High Similarity	NPC187282
0.8839	High Similarity	NPC189650
0.8837	High Similarity	NPC475352
0.8837	High Similarity	NPC229817
0.8837	High Similarity	NPC473686
0.8837	High Similarity	NPC221140
0.8837	High Similarity	NPC475220
0.8837	High Similarity	NPC87583
0.8827	High Similarity	NPC123544
0.8827	High Similarity	NPC90497
0.8827	High Similarity	NPC186113
0.8827	High Similarity	NPC85121
0.8827	High Similarity	NPC228654
0.8824	High Similarity	NPC324742
0.882	High Similarity	NPC61112
0.882	High Similarity	NPC180924
0.882	High Similarity	NPC208152
0.882	High Similarity	NPC78492
0.882	High Similarity	NPC198489
0.8812	High Similarity	NPC214632
0.8812	High Similarity	NPC135522
0.8805	High Similarity	NPC476553
0.8805	High Similarity	NPC476551
0.8805	High Similarity	NPC476552
0.8805	High Similarity	NPC258249
0.8805	High Similarity	NPC178484
0.8802	High Similarity	NPC298778
0.8797	High Similarity	NPC474052
0.8797	High Similarity	NPC329933
0.8795	High Similarity	NPC474024
0.8788	High Similarity	NPC259757
0.8788	High Similarity	NPC472051

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 NPC469664 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	407
0.1-0.2	987
0.2-0.3	1740
0.3-0.4	2690
0.4-0.5	1908
0.5-0.6	926
0.6-0.7	319
0.7-0.8	132
0.8-0.85	34
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9554	High Similarity	NPD6959	Discontinued
0.8758	High Similarity	NPD8443	Clinical (unspecified phase)
0.8718	High Similarity	NPD7390	Discontinued
0.8675	High Similarity	NPD7852	Clinical (unspecified phase)
0.858	High Similarity	NPD7819	Suspended
0.8544	High Similarity	NPD7410	Clinical (unspecified phase)
0.8544	High Similarity	NPD4378	Clinical (unspecified phase)
0.8509	High Similarity	NPD4380	Phase 2
0.8476	Intermediate Similarity	NPD7768	Phase 2
0.8466	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD6166	Phase 2
0.8452	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD6232	Discontinued
0.8412	Intermediate Similarity	NPD5844	Phase 1
0.8402	Intermediate Similarity	NPD7473	Discontinued
0.8344	Intermediate Similarity	NPD7411	Suspended
0.8304	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD2533	Approved
0.8199	Intermediate Similarity	NPD2532	Approved
0.8199	Intermediate Similarity	NPD2534	Approved
0.8182	Intermediate Similarity	NPD1934	Approved
0.8171	Intermediate Similarity	NPD8312	Approved
0.8171	Intermediate Similarity	NPD8313	Approved
0.8165	Intermediate Similarity	NPD1549	Phase 2
0.8161	Intermediate Similarity	NPD6559	Discontinued
0.8153	Intermediate Similarity	NPD2796	Approved
0.8103	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7075	Discontinued
0.8095	Intermediate Similarity	NPD3749	Approved
0.8092	Intermediate Similarity	NPD7054	Approved
0.8089	Intermediate Similarity	NPD1510	Phase 2
0.8072	Intermediate Similarity	NPD6801	Discontinued
0.8056	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD7472	Approved
0.8046	Intermediate Similarity	NPD7074	Phase 3
0.8045	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1511	Approved
0.8024	Intermediate Similarity	NPD2801	Approved
0.8011	Intermediate Similarity	NPD7808	Phase 3
0.8	Intermediate Similarity	NPD3226	Approved
0.8	Intermediate Similarity	NPD6797	Phase 2
0.7975	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD1607	Approved
0.7955	Intermediate Similarity	NPD7251	Discontinued
0.795	Intermediate Similarity	NPD3750	Approved
0.7931	Intermediate Similarity	NPD3818	Discontinued
0.7927	Intermediate Similarity	NPD1512	Approved
0.7917	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD8151	Discontinued
0.7895	Intermediate Similarity	NPD5494	Approved
0.7892	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD5402	Approved
0.787	Intermediate Similarity	NPD3817	Phase 2
0.7834	Intermediate Similarity	NPD1240	Approved
0.7812	Intermediate Similarity	NPD5408	Approved
0.7812	Intermediate Similarity	NPD5405	Approved
0.7812	Intermediate Similarity	NPD5404	Approved
0.7812	Intermediate Similarity	NPD5406	Approved
0.7778	Intermediate Similarity	NPD2800	Approved
0.7778	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5403	Approved
0.7758	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6599	Discontinued
0.7719	Intermediate Similarity	NPD3882	Suspended
0.7709	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD6100	Approved
0.7702	Intermediate Similarity	NPD6099	Approved
0.7684	Intermediate Similarity	NPD7871	Phase 2
0.7684	Intermediate Similarity	NPD7870	Phase 2
0.766	Intermediate Similarity	NPD6776	Approved
0.766	Intermediate Similarity	NPD6782	Approved
0.766	Intermediate Similarity	NPD6777	Approved
0.766	Intermediate Similarity	NPD6781	Approved
0.766	Intermediate Similarity	NPD6778	Approved
0.766	Intermediate Similarity	NPD6780	Approved
0.766	Intermediate Similarity	NPD6779	Approved
0.7654	Intermediate Similarity	NPD2346	Discontinued
0.7651	Intermediate Similarity	NPD5401	Approved
0.764	Intermediate Similarity	NPD3748	Approved
0.7632	Intermediate Similarity	NPD7697	Approved
0.7632	Intermediate Similarity	NPD7696	Phase 3
0.7632	Intermediate Similarity	NPD7698	Approved
0.7629	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD7783	Phase 2
0.7627	Intermediate Similarity	NPD7177	Discontinued
0.7622	Intermediate Similarity	NPD7003	Approved
0.7611	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD8455	Phase 2
0.7602	Intermediate Similarity	NPD1465	Phase 2
0.76	Intermediate Similarity	NPD3787	Discontinued
0.76	Intermediate Similarity	NPD5710	Approved
0.76	Intermediate Similarity	NPD5711	Approved
0.7595	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2935	Discontinued
0.7593	Intermediate Similarity	NPD1551	Phase 2
0.759	Intermediate Similarity	NPD6799	Approved
0.7561	Intermediate Similarity	NPD1243	Approved
0.756	Intermediate Similarity	NPD920	Approved
0.7541	Intermediate Similarity	NPD8150	Discontinued
0.7539	Intermediate Similarity	NPD7435	Discontinued
0.7532	Intermediate Similarity	NPD4625	Phase 3
0.7528	Intermediate Similarity	NPD3751	Discontinued
0.7516	Intermediate Similarity	NPD6651	Approved
0.7515	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD7229	Phase 3
0.75	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD4363	Phase 3
0.7487	Intermediate Similarity	NPD4360	Phase 2
0.7474	Intermediate Similarity	NPD7701	Phase 2
0.7468	Intermediate Similarity	NPD4908	Phase 1
0.7442	Intermediate Similarity	NPD37	Approved
0.744	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD2344	Approved
0.7425	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD4967	Phase 2
0.7414	Intermediate Similarity	NPD4966	Approved
0.7414	Intermediate Similarity	NPD4965	Approved
0.741	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD5953	Discontinued
0.7398	Intermediate Similarity	NPD7874	Approved
0.7398	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6273	Approved
0.7396	Intermediate Similarity	NPD6823	Phase 2
0.7394	Intermediate Similarity	NPD6535	Approved
0.7394	Intermediate Similarity	NPD6534	Approved
0.7375	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7699	Phase 2
0.7368	Intermediate Similarity	NPD7458	Discontinued
0.7368	Intermediate Similarity	NPD7700	Phase 2
0.736	Intermediate Similarity	NPD7801	Approved
0.736	Intermediate Similarity	NPD3926	Phase 2
0.7345	Intermediate Similarity	NPD1247	Approved
0.7345	Intermediate Similarity	NPD7199	Phase 2
0.7333	Intermediate Similarity	NPD7228	Approved
0.733	Intermediate Similarity	NPD6234	Discontinued
0.733	Intermediate Similarity	NPD919	Approved
0.7317	Intermediate Similarity	NPD2799	Discontinued
0.7305	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7286	Phase 2
0.7267	Intermediate Similarity	NPD2313	Discontinued
0.7262	Intermediate Similarity	NPD2309	Approved
0.7244	Intermediate Similarity	NPD1201	Approved
0.7239	Intermediate Similarity	NPD5124	Phase 1
0.7239	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD8320	Phase 1
0.7231	Intermediate Similarity	NPD8319	Approved
0.7212	Intermediate Similarity	NPD7033	Discontinued
0.7202	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4287	Approved
0.7173	Intermediate Similarity	NPD4361	Phase 2
0.7173	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1470	Approved
0.7167	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD8434	Phase 2
0.716	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6212	Phase 3
0.7158	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6213	Phase 3
0.7151	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD8285	Discontinued
0.7143	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD5760	Phase 2
0.7102	Intermediate Similarity	NPD5761	Phase 2
0.7081	Intermediate Similarity	NPD7654	Discontinued
0.7073	Intermediate Similarity	NPD1613	Approved
0.7073	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD943	Approved
0.7071	Intermediate Similarity	NPD7584	Approved
0.7062	Intermediate Similarity	NPD4288	Approved
0.7056	Intermediate Similarity	NPD8127	Discontinued
0.7055	Intermediate Similarity	NPD3268	Approved
0.7055	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1651	Approved
0.7045	Intermediate Similarity	NPD6844	Discontinued
0.7044	Intermediate Similarity	NPD4749	Approved
0.7037	Intermediate Similarity	NPD6832	Phase 2
0.7025	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1610	Phase 2
0.7019	Intermediate Similarity	NPD2798	Approved
0.7006	Intermediate Similarity	NPD4308	Phase 3
0.7	Intermediate Similarity	NPD1283	Approved
0.6989	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7240	Approved
0.6987	Remote Similarity	NPD1548	Phase 1
0.697	Remote Similarity	NPD2979	Phase 3
0.6964	Remote Similarity	NPD2438	Suspended
0.6957	Remote Similarity	NPD1203	Approved
0.6957	Remote Similarity	NPD2797	Approved
0.6951	Remote Similarity	NPD3764	Approved
0.694	Remote Similarity	NPD7784	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