NPASS Compound

Structure

NPC470333 OpenBabel07101718202D 40 45 0 0 1 0 0 0 0 0999 V2000 2.8146 0.8095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5735 1.9566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7328 -4.9628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3754 -4.2511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0176 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1584 0.9555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7149 -3.4619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2441 -2.4913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2354 0.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1118 1.4871 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.2280 1.2322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2951 -3.0058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4349 -1.8730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9965 -3.2927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6418 -2.7277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3003 -2.2678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0704 -1.3383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6809 -2.6255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0814 -2.4042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3293 -2.1674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3837 -1.6702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9306 -1.2763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5031 -0.4855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9279 0.3033 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0017 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8727 -1.4770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2390 -0.5945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4741 -0.5859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7627 0.0011 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3472 2.4345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1825 1.4369 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1717 -3.4355 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4002 -1.7275 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8438 -1.5774 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1905 -0.3760 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3825 -4.0516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5688 -3.7012 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0466 0.2049 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1850 0.8812 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 11 1 0 0 0 0 3 37 1 0 0 0 0 4 38 1 0 0 0 0 5 39 1 0 0 0 0 6 40 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 31 1 0 0 0 0 11 24 1 0 0 0 0 11 32 2 0 0 0 0 12 16 1 0 0 0 0 12 33 1 0 0 0 0 13 17 1 0 0 0 0 13 34 1 0 0 0 0 14 18 2 0 0 0 0 14 37 1 0 0 0 0 15 19 2 0 0 0 0 15 38 1 0 0 0 0 16 20 2 0 0 0 0 16 26 1 0 0 0 0 17 21 2 0 0 0 0 17 27 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 25 1 0 0 0 0 22 23 1 0 0 0 0 22 25 2 0 0 0 0 23 24 1 0 0 0 0 23 28 2 0 0 0 0 24 30 1 1 0 0 0 25 30 1 0 0 0 0 26 28 1 0 0 0 0 26 35 2 0 0 0 0 27 29 1 0 0 0 0 27 36 2 0 0 0 0 28 39 1 0 0 0 0 29 30 1 6 0 0 0 29 40 1 0 0 0 0 30 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	548.17
Volume:	534.998
LogP:	1.774
LogD:	1.048
LogS:	-5.884
# Rotatable Bonds:	7
TPSA:	148.82
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.232
Synthetic Accessibility Score:	4.92
Fsp3:	0.367
Lipinski Rule-of-5:	Accepted
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:	-5.364
MDCK Permeability:	6.723785190843046e-06
Pgp-inhibitor:	0.043
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.871
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	77.21810150146484%
Volume Distribution (VD):	1.266
Pgp-substrate:	25.700450897216797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.085
CYP1A2-substrate:	0.991
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.907
CYP2C9-inhibitor:	0.1
CYP2C9-substrate:	0.793
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.178
CYP3A4-inhibitor:	0.066
CYP3A4-substrate:	0.237

ADMET: Excretion

Clearance (CL):	1.423
Half-life (T1/2):	0.381

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.354
Drug-inuced Liver Injury (DILI):	0.929
AMES Toxicity:	0.239
Rat Oral Acute Toxicity:	0.209
Maximum Recommended Daily Dose:	0.107
Skin Sensitization:	0.168
Carcinogencity:	0.015
Eye Corrosion:	0.003
Eye Irritation:	0.121
Respiratory Toxicity:	0.086

Download Data

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

Natural Product: NPC470333

Natural Product ID:	NPC470333
*Common Name:**	Phaeosphaerin C
IUPAC Name:	n.a.
Synonyms:	Phaeosphaerin C
Standard InCHIKey:	BRUZRJKHXRRPCZ-HTKIONCRSA-N
Standard InCHI:	InChI=1S/C30H28O10/c1-10(31)9-30-24(11(2)32)23-22-20-16(26(35)28(23)39-5)12(33)7-14(37-3)18(20)19-15(38-4)8-13(34)17(21(19)25(22)30)27(36)29(30)40-6/h7-8,10,24,29,31,33-34H,9H2,1-6H3/t10?,24-,29-,30-/m1/s1
SMILES:	COc1cc(O)c2c3c1c1c(OC)cc(c4c1c1c3C(=C(C2=O)OC)[C@H]([C@]1([C@@H](C4=O)OC)CC(O)C)C(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2011656
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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	6110.0	nM	PMID[573735]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	15210.0	nM	PMID[573735]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	14350.0	nM	PMID[573735]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	19490.0	nM	PMID[573735]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	7080.0	nM	PMID[573735]

☑ 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 NPC470333 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	446
0.1-0.2	1747
0.2-0.3	3266
0.3-0.4	8442
0.4-0.5	10622
0.5-0.6	4582
0.6-0.7	5895
0.7-0.8	6729
0.8-0.85	876
0.85-0.9	87
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC470332
0.9521	High Similarity	NPC70318
0.897	High Similarity	NPC219686
0.8963	High Similarity	NPC228654
0.8902	High Similarity	NPC474637
0.8895	High Similarity	NPC470334
0.8876	High Similarity	NPC469486
0.8876	High Similarity	NPC264063
0.8848	High Similarity	NPC324736
0.8817	High Similarity	NPC472058
0.8817	High Similarity	NPC105414
0.8817	High Similarity	NPC470341
0.8817	High Similarity	NPC234497
0.8817	High Similarity	NPC324522
0.8802	High Similarity	NPC15374
0.875	High Similarity	NPC290160
0.8721	High Similarity	NPC470335
0.8721	High Similarity	NPC229051
0.8721	High Similarity	NPC470336
0.8708	High Similarity	NPC289223
0.8698	High Similarity	NPC316262
0.8698	High Similarity	NPC314653
0.8698	High Similarity	NPC469664
0.869	High Similarity	NPC315772
0.8683	High Similarity	NPC472052
0.8683	High Similarity	NPC472060
0.8683	High Similarity	NPC470342
0.8667	High Similarity	NPC226656
0.8667	High Similarity	NPC66508
0.8639	High Similarity	NPC476505
0.8631	High Similarity	NPC18380
0.8631	High Similarity	NPC472261
0.8623	High Similarity	NPC472617
0.8613	High Similarity	NPC131862
0.8605	High Similarity	NPC313717
0.8605	High Similarity	NPC315306
0.8598	High Similarity	NPC470569
0.8588	High Similarity	NPC472051
0.8588	High Similarity	NPC472057
0.858	High Similarity	NPC472059
0.8571	High Similarity	NPC313368
0.8571	High Similarity	NPC186325
0.8571	High Similarity	NPC284495
0.8571	High Similarity	NPC184326
0.8571	High Similarity	NPC472618
0.8571	High Similarity	NPC292863
0.8563	High Similarity	NPC477992
0.8563	High Similarity	NPC477991
0.8555	High Similarity	NPC473113
0.8547	High Similarity	NPC54903
0.8547	High Similarity	NPC286074
0.8538	High Similarity	NPC120857
0.8538	High Similarity	NPC477835
0.8538	High Similarity	NPC85047
0.8538	High Similarity	NPC17274
0.8537	High Similarity	NPC147735
0.8537	High Similarity	NPC470568
0.8529	High Similarity	NPC472053
0.8529	High Similarity	NPC214279
0.8521	High Similarity	NPC137232
0.8521	High Similarity	NPC273467
0.8521	High Similarity	NPC189552
0.8512	High Similarity	NPC195167
0.8512	High Similarity	NPC177650
0.8503	High Similarity	NPC474360
0.8476	Intermediate Similarity	NPC329933
0.8475	Intermediate Similarity	NPC315221
0.8466	Intermediate Similarity	NPC34802
0.8462	Intermediate Similarity	NPC476506
0.8462	Intermediate Similarity	NPC312993
0.8452	Intermediate Similarity	NPC201127
0.8448	Intermediate Similarity	NPC118128
0.8448	Intermediate Similarity	NPC477836
0.8443	Intermediate Similarity	NPC68727
0.8439	Intermediate Similarity	NPC473096
0.8439	Intermediate Similarity	NPC473095
0.8439	Intermediate Similarity	NPC20734
0.8434	Intermediate Similarity	NPC113608
0.8434	Intermediate Similarity	NPC87708
0.8434	Intermediate Similarity	NPC268992
0.8434	Intermediate Similarity	NPC470338
0.8434	Intermediate Similarity	NPC51824
0.8434	Intermediate Similarity	NPC470337
0.8434	Intermediate Similarity	NPC470340
0.8427	Intermediate Similarity	NPC182693
0.8427	Intermediate Similarity	NPC313452
0.8424	Intermediate Similarity	NPC255641
0.8424	Intermediate Similarity	NPC290954
0.8421	Intermediate Similarity	NPC100849
0.8421	Intermediate Similarity	NPC469395
0.8418	Intermediate Similarity	NPC120102
0.8415	Intermediate Similarity	NPC472841
0.8412	Intermediate Similarity	NPC312273
0.8412	Intermediate Similarity	NPC301256
0.8402	Intermediate Similarity	NPC295090
0.8402	Intermediate Similarity	NPC90497
0.8402	Intermediate Similarity	NPC51760
0.84	Intermediate Similarity	NPC469393
0.84	Intermediate Similarity	NPC154986
0.8391	Intermediate Similarity	NPC193698
0.8383	Intermediate Similarity	NPC208806
0.8383	Intermediate Similarity	NPC472211
0.8382	Intermediate Similarity	NPC286230
0.8382	Intermediate Similarity	NPC473094
0.8382	Intermediate Similarity	NPC253730
0.8373	Intermediate Similarity	NPC72958
0.8373	Intermediate Similarity	NPC232645
0.8373	Intermediate Similarity	NPC149526
0.8373	Intermediate Similarity	NPC474417
0.8373	Intermediate Similarity	NPC230848
0.8372	Intermediate Similarity	NPC169471
0.8364	Intermediate Similarity	NPC80370
0.8364	Intermediate Similarity	NPC477221
0.8363	Intermediate Similarity	NPC473012
0.8362	Intermediate Similarity	NPC5671
0.8354	Intermediate Similarity	NPC118027
0.8354	Intermediate Similarity	NPC190648
0.8354	Intermediate Similarity	NPC290194
0.8354	Intermediate Similarity	NPC56433
0.8354	Intermediate Similarity	NPC289042
0.8354	Intermediate Similarity	NPC312929
0.8354	Intermediate Similarity	NPC245584
0.8354	Intermediate Similarity	NPC52161
0.8354	Intermediate Similarity	NPC162751
0.8354	Intermediate Similarity	NPC126767
0.8353	Intermediate Similarity	NPC470810
0.8344	Intermediate Similarity	NPC28632
0.8344	Intermediate Similarity	NPC12402
0.8343	Intermediate Similarity	NPC263483
0.8343	Intermediate Similarity	NPC272196
0.8343	Intermediate Similarity	NPC475184
0.8343	Intermediate Similarity	NPC91650
0.8343	Intermediate Similarity	NPC477529
0.8333	Intermediate Similarity	NPC84266
0.8333	Intermediate Similarity	NPC300307
0.8324	Intermediate Similarity	NPC30027
0.8324	Intermediate Similarity	NPC178173
0.8324	Intermediate Similarity	NPC228209
0.8324	Intermediate Similarity	NPC251336
0.8324	Intermediate Similarity	NPC469394
0.8323	Intermediate Similarity	NPC43345
0.8323	Intermediate Similarity	NPC180944
0.8323	Intermediate Similarity	NPC154683
0.8323	Intermediate Similarity	NPC40356
0.8315	Intermediate Similarity	NPC114257
0.8315	Intermediate Similarity	NPC299149
0.8315	Intermediate Similarity	NPC277710
0.8315	Intermediate Similarity	NPC153578
0.8314	Intermediate Similarity	NPC473009
0.8314	Intermediate Similarity	NPC63438
0.8313	Intermediate Similarity	NPC294646
0.8313	Intermediate Similarity	NPC202595
0.8306	Intermediate Similarity	NPC470199
0.8306	Intermediate Similarity	NPC314459
0.8304	Intermediate Similarity	NPC61382
0.8304	Intermediate Similarity	NPC103816
0.8304	Intermediate Similarity	NPC117985
0.8303	Intermediate Similarity	NPC106524
0.8303	Intermediate Similarity	NPC290695
0.8295	Intermediate Similarity	NPC472054
0.8295	Intermediate Similarity	NPC475080
0.8294	Intermediate Similarity	NPC55443
0.8294	Intermediate Similarity	NPC105584
0.8294	Intermediate Similarity	NPC186113
0.8294	Intermediate Similarity	NPC18699
0.8293	Intermediate Similarity	NPC143685
0.8287	Intermediate Similarity	NPC240808
0.8284	Intermediate Similarity	NPC146211
0.8284	Intermediate Similarity	NPC180924
0.8284	Intermediate Similarity	NPC192587
0.8284	Intermediate Similarity	NPC69531
0.8284	Intermediate Similarity	NPC32867
0.8274	Intermediate Similarity	NPC214632
0.8274	Intermediate Similarity	NPC329844
0.8274	Intermediate Similarity	NPC155686
0.8274	Intermediate Similarity	NPC193200
0.8272	Intermediate Similarity	NPC182255
0.8272	Intermediate Similarity	NPC94076
0.8266	Intermediate Similarity	NPC474591
0.8266	Intermediate Similarity	NPC472049
0.8266	Intermediate Similarity	NPC473010
0.8266	Intermediate Similarity	NPC472784
0.8263	Intermediate Similarity	NPC476553
0.8263	Intermediate Similarity	NPC477276
0.8263	Intermediate Similarity	NPC476552
0.8263	Intermediate Similarity	NPC473131
0.8263	Intermediate Similarity	NPC470675
0.8263	Intermediate Similarity	NPC476551
0.8263	Intermediate Similarity	NPC478148
0.8258	Intermediate Similarity	NPC477683
0.8258	Intermediate Similarity	NPC477682
0.8258	Intermediate Similarity	NPC478000
0.8258	Intermediate Similarity	NPC246877
0.8256	Intermediate Similarity	NPC473011
0.8256	Intermediate Similarity	NPC475106
0.8256	Intermediate Similarity	NPC473022
0.8253	Intermediate Similarity	NPC97028
0.8253	Intermediate Similarity	NPC100985
0.8253	Intermediate Similarity	NPC288036
0.8253	Intermediate Similarity	NPC65589

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 NPC470333 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	381
0.1-0.2	1013
0.2-0.3	1819
0.3-0.4	2688
0.4-0.5	1976
0.5-0.6	836
0.6-0.7	299
0.7-0.8	129
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8743	High Similarity	NPD6959	Discontinued
0.8225	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD7473	Discontinued
0.8171	Intermediate Similarity	NPD7390	Discontinued
0.815	Intermediate Similarity	NPD6232	Discontinued
0.7955	Intermediate Similarity	NPD6166	Phase 2
0.7955	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD2532	Approved
0.7904	Intermediate Similarity	NPD2534	Approved
0.7904	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD2533	Approved
0.7892	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD4380	Phase 2
0.7836	Intermediate Similarity	NPD7411	Suspended
0.7746	Intermediate Similarity	NPD7819	Suspended
0.7746	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD5844	Phase 1
0.7714	Intermediate Similarity	NPD7075	Discontinued
0.7711	Intermediate Similarity	NPD2800	Approved
0.7692	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6801	Discontinued
0.7683	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD6651	Approved
0.7616	Intermediate Similarity	NPD3226	Approved
0.7596	Intermediate Similarity	NPD6559	Discontinued
0.7594	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD1510	Phase 2
0.7572	Intermediate Similarity	NPD6599	Discontinued
0.7561	Intermediate Similarity	NPD1607	Approved
0.756	Intermediate Similarity	NPD7003	Approved
0.7557	Intermediate Similarity	NPD3882	Suspended
0.7557	Intermediate Similarity	NPD7768	Phase 2
0.7545	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD6797	Phase 2
0.7541	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD5494	Approved
0.7514	Intermediate Similarity	NPD3749	Approved
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.7513	Intermediate Similarity	NPD6782	Approved
0.7513	Intermediate Similarity	NPD6777	Approved
0.7513	Intermediate Similarity	NPD6779	Approved
0.7513	Intermediate Similarity	NPD6778	Approved
0.7513	Intermediate Similarity	NPD6776	Approved
0.7513	Intermediate Similarity	NPD6780	Approved
0.7513	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD7251	Discontinued
0.7487	Intermediate Similarity	NPD7435	Discontinued
0.7487	Intermediate Similarity	NPD8150	Discontinued
0.7486	Intermediate Similarity	NPD1934	Approved
0.7485	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD8151	Discontinued
0.7459	Intermediate Similarity	NPD7808	Phase 3
0.7458	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD7870	Phase 2
0.7449	Intermediate Similarity	NPD7871	Phase 2
0.744	Intermediate Similarity	NPD1549	Phase 2
0.7439	Intermediate Similarity	NPD1240	Approved
0.7416	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD5402	Approved
0.7401	Intermediate Similarity	NPD3817	Phase 2
0.7398	Intermediate Similarity	NPD7698	Approved
0.7398	Intermediate Similarity	NPD7696	Phase 3
0.7398	Intermediate Similarity	NPD7697	Approved
0.7391	Intermediate Similarity	NPD7074	Phase 3
0.7386	Intermediate Similarity	NPD37	Approved
0.7377	Intermediate Similarity	NPD3818	Discontinued
0.7377	Intermediate Similarity	NPD3751	Discontinued
0.7366	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD5710	Approved
0.7348	Intermediate Similarity	NPD3787	Discontinued
0.7348	Intermediate Similarity	NPD5711	Approved
0.7345	Intermediate Similarity	NPD2801	Approved
0.7341	Intermediate Similarity	NPD6273	Approved
0.7341	Intermediate Similarity	NPD1512	Approved
0.7337	Intermediate Similarity	NPD7054	Approved
0.7321	Intermediate Similarity	NPD5406	Approved
0.7321	Intermediate Similarity	NPD5408	Approved
0.7321	Intermediate Similarity	NPD6099	Approved
0.7321	Intermediate Similarity	NPD5405	Approved
0.7321	Intermediate Similarity	NPD5404	Approved
0.7321	Intermediate Similarity	NPD2796	Approved
0.7321	Intermediate Similarity	NPD6100	Approved
0.7314	Intermediate Similarity	NPD7458	Discontinued
0.7314	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD8434	Phase 2
0.7297	Intermediate Similarity	NPD7472	Approved
0.7294	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1247	Approved
0.7278	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD7874	Approved
0.7263	Intermediate Similarity	NPD4965	Approved
0.7263	Intermediate Similarity	NPD4967	Phase 2
0.7263	Intermediate Similarity	NPD4966	Approved
0.7254	Intermediate Similarity	NPD6535	Approved
0.7254	Intermediate Similarity	NPD6534	Approved
0.7251	Intermediate Similarity	NPD3750	Approved
0.725	Intermediate Similarity	NPD7701	Phase 2
0.7247	Intermediate Similarity	NPD5760	Phase 2
0.7247	Intermediate Similarity	NPD5761	Phase 2
0.7228	Intermediate Similarity	NPD7801	Approved
0.7225	Intermediate Similarity	NPD1511	Approved
0.7225	Intermediate Similarity	NPD6799	Approved
0.7219	Intermediate Similarity	NPD2935	Discontinued
0.72	Intermediate Similarity	NPD5403	Approved
0.7198	Intermediate Similarity	NPD7199	Phase 2
0.7189	Intermediate Similarity	NPD7228	Approved
0.7186	Intermediate Similarity	NPD8319	Approved
0.7186	Intermediate Similarity	NPD8320	Phase 1
0.7182	Intermediate Similarity	NPD6234	Discontinued
0.7158	Intermediate Similarity	NPD7229	Phase 3
0.7158	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1465	Phase 2
0.7151	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7700	Phase 2
0.7143	Intermediate Similarity	NPD7699	Phase 2
0.712	Intermediate Similarity	NPD3926	Phase 2
0.7102	Intermediate Similarity	NPD920	Approved
0.709	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5401	Approved
0.7085	Intermediate Similarity	NPD6823	Phase 2
0.7076	Intermediate Similarity	NPD2346	Discontinued
0.7069	Intermediate Similarity	NPD7236	Approved
0.7062	Intermediate Similarity	NPD7239	Suspended
0.7059	Intermediate Similarity	NPD7783	Phase 2
0.7059	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD4628	Phase 3
0.7011	Intermediate Similarity	NPD8127	Discontinued
0.7006	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD919	Approved
0.6989	Remote Similarity	NPD2403	Approved
0.6977	Remote Similarity	NPD1471	Phase 3
0.6977	Remote Similarity	NPD2344	Approved
0.697	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3748	Approved
0.6954	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD1551	Phase 2
0.6915	Remote Similarity	NPD7177	Discontinued
0.6915	Remote Similarity	NPD7799	Discontinued
0.691	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1470	Approved
0.6905	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD4363	Phase 3
0.6904	Remote Similarity	NPD4360	Phase 2
0.69	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1243	Approved
0.6895	Remote Similarity	NPD5953	Discontinued
0.6893	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD4908	Phase 1
0.6878	Remote Similarity	NPD7286	Phase 2
0.6871	Remote Similarity	NPD1201	Approved
0.686	Remote Similarity	NPD651	Clinical (unspecified phase)
0.686	Remote Similarity	NPD2799	Discontinued
0.6859	Remote Similarity	NPD7240	Approved
0.6859	Remote Similarity	NPD6765	Approved
0.6859	Remote Similarity	NPD6764	Approved
0.6853	Remote Similarity	NPD6212	Phase 3
0.6853	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6213	Phase 3
0.6845	Remote Similarity	NPD4625	Phase 3
0.6825	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD943	Approved
0.6818	Remote Similarity	NPD2309	Approved
0.6814	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.678	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD8455	Phase 2
0.6771	Remote Similarity	NPD7685	Pre-registration
0.6763	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD2932	Approved
0.6748	Remote Similarity	NPD3019	Approved
0.6747	Remote Similarity	NPD1283	Approved
0.6747	Remote Similarity	NPD1876	Approved
0.6743	Remote Similarity	NPD8067	Phase 3
0.6727	Remote Similarity	NPD3972	Approved
0.6723	Remote Similarity	NPD6190	Approved
0.6718	Remote Similarity	NPD6785	Approved
0.6718	Remote Similarity	NPD6784	Approved
0.6706	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD3764	Approved
0.6703	Remote Similarity	NPD7058	Phase 2
0.6703	Remote Similarity	NPD7057	Phase 3
0.6701	Remote Similarity	NPD4287	Approved
0.67	Remote Similarity	NPD4361	Phase 2
0.67	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1651	Approved
0.6686	Remote Similarity	NPD5763	Approved
0.6686	Remote Similarity	NPD5762	Approved
0.6685	Remote Similarity	NPD3300	Phase 2
0.6683	Remote Similarity	NPD8285	Discontinued

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