NPASS Compound

Structure

NPC470336 OpenBabel07101718202D 41 47 0 0 1 0 0 0 0 0999 V2000 0.0370 -2.8482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1130 1.1321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4080 -4.6475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5537 -4.6900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8814 -1.7611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6786 0.4624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2104 -3.2203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9287 -2.1148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8407 -1.4134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0247 -1.8988 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4315 0.2376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2887 -3.1124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9501 -1.6022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6060 -2.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4741 -2.3526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5156 -2.6549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5168 -1.3273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6001 -2.3867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0408 -2.0778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0837 -2.2348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0741 -1.5406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0196 -1.5057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6748 -1.1796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6439 -1.1968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1790 -2.3459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6262 -0.8482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2432 -1.6169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3198 -0.4640 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8284 -0.4640 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8160 -0.4854 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3653 0.0662 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8722 -3.8615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7914 -1.1621 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9565 -2.8909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5519 -0.6369 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3262 -3.7016 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3950 -4.2499 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1040 -1.2161 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7318 0.3914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8037 -1.4348 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 2 11 1 0 0 0 0 3 36 1 0 0 0 0 4 37 1 0 0 0 0 5 38 1 0 0 0 0 6 39 1 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 10 1 1 6 0 0 0 10 40 1 0 0 0 0 11 31 2 0 0 0 0 12 16 1 0 0 0 0 12 32 1 0 0 0 0 13 17 1 0 0 0 0 13 33 1 0 0 0 0 14 18 2 0 0 0 0 14 36 1 0 0 0 0 15 19 2 0 0 0 0 15 37 1 0 0 0 0 16 20 2 0 0 0 0 16 25 1 0 0 0 0 17 21 2 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 23 29 1 0 0 0 0 24 27 2 0 0 0 0 24 30 1 0 0 0 0 25 27 1 0 0 0 0 25 34 2 0 0 0 0 26 28 1 0 0 0 0 26 35 2 0 0 0 0 27 38 1 0 0 0 0 28 29 1 6 0 0 0 28 39 1 0 0 0 0 29 9 1 6 0 0 0 29 41 1 0 0 0 0 30 11 1 1 0 0 0 30 40 1 0 0 0 0 30 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	562.15
Volume:	535.232
LogP:	2.93
LogD:	1.655
LogS:	-5.71
# Rotatable Bonds:	5
TPSA:	147.05
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.273
Synthetic Accessibility Score:	6.186
Fsp3:	0.367
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.248
MDCK Permeability:	1.1070676919189282e-05
Pgp-inhibitor:	0.696
Pgp-substrate:	0.97
Human Intestinal Absorption (HIA):	0.724
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	74.34740447998047%
Volume Distribution (VD):	1.155
Pgp-substrate:	23.11285400390625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.082
CYP1A2-substrate:	0.998
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.926
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.153
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.082
CYP3A4-substrate:	0.677

ADMET: Excretion

Clearance (CL):	1.386
Half-life (T1/2):	0.446

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.816
Drug-inuced Liver Injury (DILI):	0.985
AMES Toxicity:	0.541
Rat Oral Acute Toxicity:	0.678
Maximum Recommended Daily Dose:	0.176
Skin Sensitization:	0.828
Carcinogencity:	0.938
Eye Corrosion:	0.004
Eye Irritation:	0.229
Respiratory Toxicity:	0.346

Download Data

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

Natural Product: NPC470336

Natural Product ID:	NPC470336
*Common Name:**	Phaeosphaerin F
IUPAC Name:	n.a.
Synonyms:	Phaeosphaerin F
Standard InCHIKey:	UGUJKMQYMPNTTH-TYQMDDDJSA-N
Standard InCHI:	InChI=1S/C30H26O11/c1-10-9-29-23-21-17(26(35)28(29)39-6)13(33)8-15(37-4)19(21)18-14(36-3)7-12(32)16-20(18)22(23)24(27(38-5)25(16)34)30(40-10,41-29)11(2)31/h7-8,10,28,32-33H,9H2,1-6H3/t10-,28+,29+,30+/m0/s1
SMILES:	COc1cc(O)c2c3c1c1c(OC)cc(c4c1c1c3C(=C(C2=O)OC)[C@]2(O[C@]1([C@@H](C4=O)OC)C[C@@H](O2)C)C(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011659
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002903] Perylenequinones

*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
NPO32545	Phaeosphaeria sp.	Species	Phaeosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18570471]
NPO32545	Phaeosphaeria sp.	Species	Phaeosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22276650]
NPO32545	Phaeosphaeria sp.	Species	Phaeosphaeriaceae	Eukaryota	isolated from living stems and leaves of a Sedum sp.	Motilleja, Albacete, Spain	n.a.	PMID[23259972]

☑ 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

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	5450.0	nM	PMID[507978]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	16660.0	nM	PMID[507978]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	11840.0	nM	PMID[507978]

☑ 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 NPC470336 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	424
0.1-0.2	1711
0.2-0.3	3471
0.3-0.4	8583
0.4-0.5	9640
0.5-0.6	4627
0.6-0.7	5765
0.7-0.8	6089
0.8-0.85	2213
0.85-0.9	165
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470335
0.9578	High Similarity	NPC470334
0.9217	High Similarity	NPC264063
0.9217	High Similarity	NPC469486
0.9167	High Similarity	NPC131862
0.9167	High Similarity	NPC229051
0.9123	High Similarity	NPC315221
0.907	High Similarity	NPC313452
0.903	High Similarity	NPC15374
0.897	High Similarity	NPC219686
0.8963	High Similarity	NPC228654
0.896	High Similarity	NPC470332
0.8953	High Similarity	NPC299149
0.8953	High Similarity	NPC153578
0.8953	High Similarity	NPC114257
0.8953	High Similarity	NPC277710
0.8941	High Similarity	NPC213052
0.8876	High Similarity	NPC259905
0.8869	High Similarity	NPC178851
0.8857	High Similarity	NPC87583
0.8837	High Similarity	NPC475246
0.8837	High Similarity	NPC46958
0.883	High Similarity	NPC154986
0.8824	High Similarity	NPC8704
0.8824	High Similarity	NPC287884
0.8824	High Similarity	NPC298778
0.882	High Similarity	NPC470199
0.882	High Similarity	NPC314459
0.8817	High Similarity	NPC472058
0.8817	High Similarity	NPC470341
0.8817	High Similarity	NPC324522
0.8817	High Similarity	NPC105414
0.8817	High Similarity	NPC234497
0.8814	High Similarity	NPC314672
0.8786	High Similarity	NPC5671
0.8786	High Similarity	NPC477682
0.8786	High Similarity	NPC477683
0.8779	High Similarity	NPC3718
0.8779	High Similarity	NPC63105
0.8772	High Similarity	NPC5029
0.8772	High Similarity	NPC473113
0.8772	High Similarity	NPC76128
0.8772	High Similarity	NPC111536
0.8772	High Similarity	NPC30432
0.8772	High Similarity	NPC271385
0.8765	High Similarity	NPC470206
0.8765	High Similarity	NPC470207
0.8765	High Similarity	NPC473095
0.8765	High Similarity	NPC473096
0.8757	High Similarity	NPC477835
0.8757	High Similarity	NPC178173
0.875	High Similarity	NPC475352
0.875	High Similarity	NPC290160
0.875	High Similarity	NPC229817
0.875	High Similarity	NPC473686
0.875	High Similarity	NPC475220
0.875	High Similarity	NPC221140
0.8743	High Similarity	NPC475662
0.8743	High Similarity	NPC293227
0.8743	High Similarity	NPC473717
0.8743	High Similarity	NPC473631
0.8743	High Similarity	NPC18380
0.8743	High Similarity	NPC472261
0.8743	High Similarity	NPC137232
0.8736	High Similarity	NPC70318
0.8736	High Similarity	NPC244903
0.8735	High Similarity	NPC51760
0.8728	High Similarity	NPC475233
0.8722	High Similarity	NPC470197
0.8722	High Similarity	NPC470195
0.8722	High Similarity	NPC470196
0.8722	High Similarity	NPC470194
0.8722	High Similarity	NPC316274
0.8722	High Similarity	NPC282474
0.8722	High Similarity	NPC470198
0.8722	High Similarity	NPC470193
0.8722	High Similarity	NPC470200
0.8721	High Similarity	NPC470333
0.8721	High Similarity	NPC85368
0.8706	High Similarity	NPC292233
0.8706	High Similarity	NPC473094
0.8706	High Similarity	NPC474024
0.8701	High Similarity	NPC105591
0.8698	High Similarity	NPC469664
0.8686	High Similarity	NPC477860
0.8686	High Similarity	NPC475161
0.8683	High Similarity	NPC186325
0.8683	High Similarity	NPC184326
0.8683	High Similarity	NPC292863
0.8678	High Similarity	NPC47191
0.8678	High Similarity	NPC246877
0.8671	High Similarity	NPC474345
0.8671	High Similarity	NPC470667
0.8671	High Similarity	NPC68381
0.8671	High Similarity	NPC108202
0.8671	High Similarity	NPC294629
0.8663	High Similarity	NPC4200
0.8663	High Similarity	NPC477529
0.8663	High Similarity	NPC477836
0.8663	High Similarity	NPC294501
0.8659	High Similarity	NPC48474
0.8655	High Similarity	NPC175477
0.8655	High Similarity	NPC300307
0.8655	High Similarity	NPC473202
0.8652	High Similarity	NPC205721
0.8647	High Similarity	NPC272502
0.8631	High Similarity	NPC273467
0.8631	High Similarity	NPC117985
0.8631	High Similarity	NPC189552
0.8629	High Similarity	NPC245059
0.8629	High Similarity	NPC212290
0.8629	High Similarity	NPC84494
0.8623	High Similarity	NPC177650
0.8623	High Similarity	NPC195167
0.8623	High Similarity	NPC324736
0.8613	High Similarity	NPC98776
0.8613	High Similarity	NPC17105
0.8613	High Similarity	NPC73899
0.8613	High Similarity	NPC474276
0.8613	High Similarity	NPC203751
0.8613	High Similarity	NPC472054
0.8613	High Similarity	NPC147363
0.8605	High Similarity	NPC477571
0.8605	High Similarity	NPC477573
0.8605	High Similarity	NPC478021
0.8605	High Similarity	NPC477572
0.8603	High Similarity	NPC201814
0.8598	High Similarity	NPC149526
0.8598	High Similarity	NPC232645
0.8598	High Similarity	NPC72958
0.8598	High Similarity	NPC474417
0.8596	High Similarity	NPC472622
0.8596	High Similarity	NPC64755
0.8588	High Similarity	NPC75574
0.8588	High Similarity	NPC472057
0.8588	High Similarity	NPC472049
0.8588	High Similarity	NPC478020
0.8588	High Similarity	NPC478022
0.8588	High Similarity	NPC472051
0.858	High Similarity	NPC34802
0.858	High Similarity	NPC470452
0.858	High Similarity	NPC470453
0.858	High Similarity	NPC208069
0.858	High Similarity	NPC259834
0.858	High Similarity	NPC164047
0.858	High Similarity	NPC472059
0.858	High Similarity	NPC470448
0.858	High Similarity	NPC216752
0.8571	High Similarity	NPC472060
0.8571	High Similarity	NPC472052
0.8571	High Similarity	NPC312993
0.8571	High Similarity	NPC472055
0.8571	High Similarity	NPC470342
0.8571	High Similarity	NPC470810
0.8563	High Similarity	NPC470454
0.8563	High Similarity	NPC146803
0.8563	High Similarity	NPC98667
0.8563	High Similarity	NPC294149
0.8563	High Similarity	NPC232412
0.8563	High Similarity	NPC86809
0.8563	High Similarity	NPC477992
0.8563	High Similarity	NPC246466
0.8563	High Similarity	NPC477991
0.8563	High Similarity	NPC186800
0.8563	High Similarity	NPC199533
0.8556	High Similarity	NPC264302
0.8555	High Similarity	NPC472620
0.8555	High Similarity	NPC270027
0.8555	High Similarity	NPC186847
0.8555	High Similarity	NPC257667
0.8555	High Similarity	NPC472454
0.8554	High Similarity	NPC226656
0.8554	High Similarity	NPC134171
0.8554	High Similarity	NPC66508
0.8554	High Similarity	NPC300668
0.8547	High Similarity	NPC270578
0.8547	High Similarity	NPC222455
0.8547	High Similarity	NPC52382
0.8547	High Similarity	NPC177480
0.8547	High Similarity	NPC326877
0.8547	High Similarity	NPC472619
0.8547	High Similarity	NPC5319
0.8547	High Similarity	NPC137460
0.8545	High Similarity	NPC87708
0.8538	High Similarity	NPC43319
0.8538	High Similarity	NPC82330
0.8538	High Similarity	NPC472621
0.8537	High Similarity	NPC325983
0.8529	High Similarity	NPC472053
0.8529	High Similarity	NPC66087
0.8529	High Similarity	NPC183672
0.8529	High Similarity	NPC278419
0.8529	High Similarity	NPC197168
0.8529	High Similarity	NPC179198
0.8529	High Similarity	NPC63438
0.8523	High Similarity	NPC121888
0.8521	High Similarity	NPC478134
0.8514	High Similarity	NPC289876
0.8514	High Similarity	NPC469345
0.8514	High Similarity	NPC312630

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 NPC470336 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	972
0.2-0.3	1824
0.3-0.4	2704
0.4-0.5	1889
0.5-0.6	907
0.6-0.7	325
0.7-0.8	118
0.8-0.85	42
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9085	High Similarity	NPD6959	Discontinued
0.8596	High Similarity	NPD7879	Clinical (unspecified phase)
0.8547	High Similarity	NPD7804	Clinical (unspecified phase)
0.848	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.848	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.848	Intermediate Similarity	NPD6166	Phase 2
0.8471	Intermediate Similarity	NPD6232	Discontinued
0.8448	Intermediate Similarity	NPD6797	Phase 2
0.843	Intermediate Similarity	NPD7473	Discontinued
0.84	Intermediate Similarity	NPD7251	Discontinued
0.8352	Intermediate Similarity	NPD7808	Phase 3
0.8286	Intermediate Similarity	NPD7074	Phase 3
0.8278	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD7075	Discontinued
0.8229	Intermediate Similarity	NPD7054	Approved
0.8229	Intermediate Similarity	NPD5844	Phase 1
0.8211	Intermediate Similarity	NPD8151	Discontinued
0.8204	Intermediate Similarity	NPD4380	Phase 2
0.8192	Intermediate Similarity	NPD6559	Discontinued
0.8182	Intermediate Similarity	NPD7472	Approved
0.8172	Intermediate Similarity	NPD6781	Approved
0.8172	Intermediate Similarity	NPD6778	Approved
0.8172	Intermediate Similarity	NPD6779	Approved
0.8172	Intermediate Similarity	NPD6782	Approved
0.8172	Intermediate Similarity	NPD6780	Approved
0.8172	Intermediate Similarity	NPD6776	Approved
0.8172	Intermediate Similarity	NPD6777	Approved
0.8171	Intermediate Similarity	NPD3751	Discontinued
0.8171	Intermediate Similarity	NPD7390	Discontinued
0.8166	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD3787	Discontinued
0.8138	Intermediate Similarity	NPD7697	Approved
0.8138	Intermediate Similarity	NPD7696	Phase 3
0.8138	Intermediate Similarity	NPD7435	Discontinued
0.8138	Intermediate Similarity	NPD7698	Approved
0.8129	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD8313	Approved
0.8101	Intermediate Similarity	NPD8312	Approved
0.8095	Intermediate Similarity	NPD7871	Phase 2
0.8095	Intermediate Similarity	NPD7870	Phase 2
0.8059	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD7819	Suspended
0.8057	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8034	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6801	Discontinued
0.8	Intermediate Similarity	NPD1934	Approved
0.7969	Intermediate Similarity	NPD7701	Phase 2
0.7965	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7411	Suspended
0.7907	Intermediate Similarity	NPD3817	Phase 2
0.7904	Intermediate Similarity	NPD2532	Approved
0.7904	Intermediate Similarity	NPD2534	Approved
0.7904	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD2533	Approved
0.7903	Intermediate Similarity	NPD6535	Approved
0.7903	Intermediate Similarity	NPD6534	Approved
0.7887	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD7874	Approved
0.7872	Intermediate Similarity	NPD7700	Phase 2
0.7872	Intermediate Similarity	NPD7699	Phase 2
0.7869	Intermediate Similarity	NPD8150	Discontinued
0.7865	Intermediate Similarity	NPD3818	Discontinued
0.7829	Intermediate Similarity	NPD5494	Approved
0.7812	Intermediate Similarity	NPD8320	Phase 1
0.7812	Intermediate Similarity	NPD8319	Approved
0.7778	Intermediate Similarity	NPD6599	Discontinued
0.7765	Intermediate Similarity	NPD7228	Approved
0.7759	Intermediate Similarity	NPD3882	Suspended
0.7759	Intermediate Similarity	NPD7768	Phase 2
0.7755	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD7783	Phase 2
0.7755	Intermediate Similarity	NPD7801	Approved
0.7746	Intermediate Similarity	NPD1465	Phase 2
0.7717	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD3749	Approved
0.7708	Intermediate Similarity	NPD6823	Phase 2
0.7697	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD37	Approved
0.767	Intermediate Similarity	NPD6234	Discontinued
0.7657	Intermediate Similarity	NPD4965	Approved
0.7657	Intermediate Similarity	NPD4967	Phase 2
0.7657	Intermediate Similarity	NPD4966	Approved
0.7651	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1549	Phase 2
0.7647	Intermediate Similarity	NPD1512	Approved
0.7644	Intermediate Similarity	NPD2801	Approved
0.7633	Intermediate Similarity	NPD6799	Approved
0.7616	Intermediate Similarity	NPD7458	Discontinued
0.76	Intermediate Similarity	NPD5402	Approved
0.7598	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1510	Phase 2
0.7561	Intermediate Similarity	NPD1607	Approved
0.7543	Intermediate Similarity	NPD8455	Phase 2
0.7529	Intermediate Similarity	NPD1511	Approved
0.7514	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3750	Approved
0.7444	Intermediate Similarity	NPD5710	Approved
0.7444	Intermediate Similarity	NPD5711	Approved
0.7439	Intermediate Similarity	NPD1240	Approved
0.7425	Intermediate Similarity	NPD5406	Approved
0.7425	Intermediate Similarity	NPD5408	Approved
0.7425	Intermediate Similarity	NPD5404	Approved
0.7425	Intermediate Similarity	NPD2796	Approved
0.7425	Intermediate Similarity	NPD5405	Approved
0.7414	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7240	Approved
0.7396	Intermediate Similarity	NPD2800	Approved
0.7389	Intermediate Similarity	NPD7199	Phase 2
0.7384	Intermediate Similarity	NPD5401	Approved
0.7382	Intermediate Similarity	NPD6213	Phase 3
0.7382	Intermediate Similarity	NPD6212	Phase 3
0.7382	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD919	Approved
0.7353	Intermediate Similarity	NPD7003	Approved
0.7349	Intermediate Similarity	NPD6651	Approved
0.7321	Intermediate Similarity	NPD6099	Approved
0.7321	Intermediate Similarity	NPD2935	Discontinued
0.7321	Intermediate Similarity	NPD6100	Approved
0.7308	Intermediate Similarity	NPD3926	Phase 2
0.7294	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1247	Approved
0.7283	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2346	Discontinued
0.7268	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD8434	Phase 2
0.716	Intermediate Similarity	NPD3748	Approved
0.7152	Intermediate Similarity	NPD4625	Phase 3
0.7151	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4628	Phase 3
0.7118	Intermediate Similarity	NPD1551	Phase 2
0.7114	Intermediate Similarity	NPD7584	Approved
0.711	Intermediate Similarity	NPD6190	Approved
0.7108	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD920	Approved
0.7097	Intermediate Similarity	NPD7177	Discontinued
0.7075	Intermediate Similarity	NPD8059	Phase 3
0.7075	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7229	Phase 3
0.7037	Intermediate Similarity	NPD7685	Pre-registration
0.702	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1243	Approved
0.6994	Remote Similarity	NPD6674	Discontinued
0.6989	Remote Similarity	NPD2403	Approved
0.6988	Remote Similarity	NPD4908	Phase 1
0.6984	Remote Similarity	NPD5953	Discontinued
0.6968	Remote Similarity	NPD7286	Phase 2
0.6965	Remote Similarity	NPD7680	Approved
0.6959	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7930	Approved
0.6935	Remote Similarity	NPD8285	Discontinued
0.6923	Remote Similarity	NPD4060	Phase 1
0.6923	Remote Similarity	NPD943	Approved
0.6919	Remote Similarity	NPD2438	Suspended
0.6915	Remote Similarity	NPD7799	Discontinued
0.6911	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6798	Discontinued
0.6904	Remote Similarity	NPD4363	Phase 3
0.6904	Remote Similarity	NPD4360	Phase 2
0.6902	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD230	Phase 1
0.6879	Remote Similarity	NPD2344	Approved
0.6875	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3300	Phase 2
0.6872	Remote Similarity	NPD4287	Approved
0.6871	Remote Similarity	NPD1201	Approved
0.6867	Remote Similarity	NPD2798	Approved
0.686	Remote Similarity	NPD2799	Discontinued
0.6854	Remote Similarity	NPD6273	Approved
0.6854	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.684	Remote Similarity	NPD8366	Approved
0.6824	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1613	Approved
0.682	Remote Similarity	NPD8067	Phase 3
0.6807	Remote Similarity	NPD1470	Approved
0.6805	Remote Similarity	NPD3764	Approved
0.6805	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7097	Phase 1
0.6788	Remote Similarity	NPD4749	Approved
0.6784	Remote Similarity	NPD1933	Approved
0.6782	Remote Similarity	NPD7266	Discontinued
0.6778	Remote Similarity	NPD1653	Approved
0.6765	Remote Similarity	NPD6233	Phase 2
0.6761	Remote Similarity	NPD8166	Discontinued
0.6761	Remote Similarity	NPD7907	Approved
0.6753	Remote Similarity	NPD7090	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