NPASS Compound

Structure

CID219686 OpenBabel06191716012D 40 45 0 0 1 0 0 0 0 0999 V2000 1.9177 -2.1639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5387 -2.5715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3823 2.7945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8439 3.5800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9127 -3.3511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6365 0.0955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3705 0.8918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9758 2.0961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3210 -1.8097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5555 -1.2896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9117 -1.4687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3746 -0.0467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4680 1.6829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5513 1.3793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6155 1.9567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9068 -0.5175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5536 -0.5207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4744 1.0282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7303 0.9053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9054 1.3696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7229 -0.0464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0884 -0.0426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0893 0.8985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4977 -0.3837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3212 -1.0425 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5434 -1.4676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0104 0.6283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7274 -1.9387 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 -0.6622 -1.6332 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1316 -0.5387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1116 -0.4701 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3887 2.0851 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2813 -1.8989 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8697 1.0249 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2122 -1.9954 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5575 2.3272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1983 2.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7277 -2.8801 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8458 -0.4246 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 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 11 1 0 0 0 0 9 30 1 0 0 0 0 10 25 1 0 0 0 0 10 31 2 0 0 0 0 11 16 1 0 0 0 0 11 28 2 0 0 0 0 12 17 1 0 0 0 0 12 32 1 0 0 0 0 13 18 1 0 0 0 0 13 33 1 0 0 0 0 14 19 2 0 0 0 0 14 37 1 0 0 0 0 15 20 2 0 0 0 0 15 38 1 0 0 0 0 16 21 1 0 0 0 0 16 22 2 0 0 0 0 17 21 2 0 0 0 0 17 26 1 0 0 0 0 18 23 2 0 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 23 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 24 25 1 0 0 0 0 24 29 2 0 0 0 0 25 30 1 1 0 0 0 26 28 1 0 0 0 0 26 34 2 0 0 0 0 27 29 1 0 0 0 0 27 35 2 0 0 0 0 28 39 1 0 0 0 0 29 40 1 0 0 0 0 30 2 1 6 0 0 0 30 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	546.15
Volume:	532.362
LogP:	4.666
LogD:	2.075
LogS:	-5.855
# Rotatable Bonds:	5
TPSA:	148.82
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.221
Synthetic Accessibility Score:	4.317
Fsp3:	0.3
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:	-4.995
MDCK Permeability:	9.44474322750466e-06
Pgp-inhibitor:	0.65
Pgp-substrate:	0.916
Human Intestinal Absorption (HIA):	0.865
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	71.94271087646484%
Volume Distribution (VD):	0.969
Pgp-substrate:	44.19633865356445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.089
CYP1A2-substrate:	0.992
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.868
CYP2C9-inhibitor:	0.351
CYP2C9-substrate:	0.844
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.193
CYP3A4-inhibitor:	0.061
CYP3A4-substrate:	0.236

ADMET: Excretion

Clearance (CL):	1.488
Half-life (T1/2):	0.294

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.815
AMES Toxicity:	0.189
Rat Oral Acute Toxicity:	0.109
Maximum Recommended Daily Dose:	0.056
Skin Sensitization:	0.148
Carcinogencity:	0.013
Eye Corrosion:	0.004
Eye Irritation:	0.569
Respiratory Toxicity:	0.055

Download Data

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

Natural Product: NPC219686

Natural Product ID:	NPC219686
*Common Name:**	Hypocrellin A
IUPAC Name:	n.a.
Synonyms:	Hypocrellin A; Rel-Hypocrellin A
Standard InCHIKey:	BQJKVFXDDMQLBE-RNAHPLFWSA-N
Standard InCHI:	InChI=1S/C30H26O10/c1-10(31)25-24-22-16-11(9-30(25,2)36)28(39-5)26(34)17-12(32)7-14(37-3)19(21(16)17)20-15(38-4)8-13(33)18(23(20)22)27(35)29(24)40-6/h7-8,25,32-33,36H,9H2,1-6H3/t25-,30+/m1/s1
SMILES:	CC(=O)[C@@H]1C2=C(C(=O)c3c(cc(c4c5c(cc(c6c5c(C(=C(C6=O)OC)C[C@]1(C)O)c2c34)O)OC)OC)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL330348
PubChem CID:	NA
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
ED50	12
IC50	2
Others	3

Activity Type	# Activity
Cell Line	14
Individual Protein	2
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	4.64	mg ml-1	PMID[482579]
NPT180	Cell Line	HCT-8	Homo sapiens	ED50	=	3.18	mg ml-1	PMID[482579]
NPT1178	Cell Line	KB 3-1	Homo sapiens	ED50	=	0.55	mg ml-1	PMID[482579]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.39	mg ml-1	PMID[482579]
NPT189	Cell Line	Vero	Chlorocebus aethiops	ED50	=	5.0	mg ml-1	PMID[482579]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	2.1	mg ml-1	PMID[482580]
NPT180	Cell Line	HCT-8	Homo sapiens	ED50	=	0.55	mg ml-1	PMID[482580]
NPT1178	Cell Line	KB 3-1	Homo sapiens	ED50	=	5.5	mg ml-1	PMID[482580]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.54	mg ml-1	PMID[482580]
NPT189	Cell Line	Vero	Chlorocebus aethiops	ED50	=	5.0	mg ml-1	PMID[482580]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	7470.0	nM	PMID[482581]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	550.0	nM	PMID[482581]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	5.56	%	PMID[482582]
NPT727	Protein Family	Protein kinase C, PKC; classical/novel	Homo sapiens	PKC	=	44.0	uM	PMID[482580]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	1.53	%	PMID[482582]

☑ 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 NPC219686 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	471
0.1-0.2	1989
0.2-0.3	4241
0.3-0.4	10781
0.4-0.5	7843
0.5-0.6	4520
0.6-0.7	5441
0.7-0.8	6337
0.8-0.85	950
0.85-0.9	105
0.9-0.95	17
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9739	High Similarity	NPC228654
0.9255	High Similarity	NPC264063
0.9255	High Similarity	NPC469486
0.9172	High Similarity	NPC474637
0.9091	High Similarity	NPC329933
0.9085	High Similarity	NPC34802
0.9085	High Similarity	NPC131862
0.9085	High Similarity	NPC229051
0.897	High Similarity	NPC470335
0.897	High Similarity	NPC470333
0.897	High Similarity	NPC470336
0.8957	High Similarity	NPC324522
0.8957	High Similarity	NPC105414
0.8957	High Similarity	NPC470341
0.8957	High Similarity	NPC472058
0.8957	High Similarity	NPC234497
0.8944	High Similarity	NPC15374
0.8938	High Similarity	NPC186325
0.8938	High Similarity	NPC470342
0.8938	High Similarity	NPC472060
0.8938	High Similarity	NPC472052
0.8924	High Similarity	NPC66508
0.8924	High Similarity	NPC226656
0.8903	High Similarity	NPC472841
0.8882	High Similarity	NPC189552
0.8882	High Similarity	NPC273467
0.8875	High Similarity	NPC177650
0.8875	High Similarity	NPC324736
0.8861	High Similarity	NPC329844
0.8854	High Similarity	NPC474417
0.8854	High Similarity	NPC149526
0.8834	High Similarity	NPC472057
0.8834	High Similarity	NPC472051
0.8827	High Similarity	NPC472059
0.8824	High Similarity	NPC84266
0.882	High Similarity	NPC312993
0.881	High Similarity	NPC470334
0.8773	High Similarity	NPC290160
0.8773	High Similarity	NPC472053
0.8765	High Similarity	NPC18380
0.8765	High Similarity	NPC137232
0.8765	High Similarity	NPC472261
0.8758	High Similarity	NPC182255
0.8758	High Similarity	NPC94076
0.8757	High Similarity	NPC70318
0.8734	High Similarity	NPC478148
0.8726	High Similarity	NPC97029
0.8726	High Similarity	NPC158338
0.8726	High Similarity	NPC97028
0.8726	High Similarity	NPC288036
0.8726	High Similarity	NPC65589
0.8726	High Similarity	NPC80370
0.8726	High Similarity	NPC100985
0.872	High Similarity	NPC469664
0.8718	High Similarity	NPC245584
0.8718	High Similarity	NPC289042
0.8718	High Similarity	NPC118027
0.8718	High Similarity	NPC190648
0.8718	High Similarity	NPC56433
0.8718	High Similarity	NPC126767
0.8718	High Similarity	NPC312929
0.871	High Similarity	NPC28632
0.8704	High Similarity	NPC184326
0.8704	High Similarity	NPC292863
0.8693	High Similarity	NPC110810
0.869	High Similarity	NPC477992
0.869	High Similarity	NPC477991
0.8679	High Similarity	NPC87708
0.8671	High Similarity	NPC294646
0.8671	High Similarity	NPC147735
0.8671	High Similarity	NPC470568
0.8662	High Similarity	NPC27221
0.8662	High Similarity	NPC256672
0.8662	High Similarity	NPC7025
0.8655	High Similarity	NPC470332
0.865	High Similarity	NPC318081
0.8642	High Similarity	NPC195167
0.8642	High Similarity	NPC55443
0.8642	High Similarity	NPC18699
0.8636	High Similarity	NPC232021
0.8636	High Similarity	NPC40118
0.8636	High Similarity	NPC126534
0.8634	High Similarity	NPC146211
0.8634	High Similarity	NPC474360
0.8631	High Similarity	NPC154986
0.8625	High Similarity	NPC210942
0.8625	High Similarity	NPC169990
0.8616	High Similarity	NPC72958
0.8616	High Similarity	NPC230848
0.8616	High Similarity	NPC232645
0.8616	High Similarity	NPC470569
0.8599	High Similarity	NPC22005
0.8599	High Similarity	NPC259632
0.8599	High Similarity	NPC7943
0.8599	High Similarity	NPC123202
0.859	High Similarity	NPC328623
0.8589	High Similarity	NPC284495
0.8589	High Similarity	NPC472618
0.8581	High Similarity	NPC297600
0.858	High Similarity	NPC272196
0.858	High Similarity	NPC201127
0.8571	High Similarity	NPC254351
0.8571	High Similarity	NPC473113
0.8571	High Similarity	NPC68727
0.8571	High Similarity	NPC265178
0.8571	High Similarity	NPC275575
0.8563	High Similarity	NPC54903
0.8563	High Similarity	NPC286074
0.8562	High Similarity	NPC113608
0.8562	High Similarity	NPC470338
0.8562	High Similarity	NPC40356
0.8562	High Similarity	NPC470340
0.8562	High Similarity	NPC217447
0.8562	High Similarity	NPC154683
0.8562	High Similarity	NPC45934
0.8562	High Similarity	NPC142527
0.8562	High Similarity	NPC268992
0.8562	High Similarity	NPC470337
0.8562	High Similarity	NPC51824
0.8554	High Similarity	NPC178173
0.8554	High Similarity	NPC477835
0.8554	High Similarity	NPC30027
0.8553	High Similarity	NPC255641
0.8553	High Similarity	NPC290954
0.8545	High Similarity	NPC159508
0.8537	High Similarity	NPC61382
0.8537	High Similarity	NPC103816
0.8535	High Similarity	NPC473135
0.8535	High Similarity	NPC225173
0.8535	High Similarity	NPC470676
0.8535	High Similarity	NPC163846
0.8535	High Similarity	NPC473132
0.8528	High Similarity	NPC51760
0.8528	High Similarity	NPC472617
0.8528	High Similarity	NPC474373
0.8526	High Similarity	NPC227841
0.8526	High Similarity	NPC19896
0.8519	High Similarity	NPC180924
0.8509	High Similarity	NPC71061
0.8509	High Similarity	NPC290830
0.8509	High Similarity	NPC303485
0.8509	High Similarity	NPC72425
0.8509	High Similarity	NPC155686
0.8509	High Similarity	NPC194593
0.8503	High Similarity	NPC253730
0.8503	High Similarity	NPC76647
0.8503	High Similarity	NPC286230
0.8494	Intermediate Similarity	NPC316262
0.8494	Intermediate Similarity	NPC314653
0.8494	Intermediate Similarity	NPC169471
0.8491	Intermediate Similarity	NPC269420
0.8485	Intermediate Similarity	NPC475106
0.8481	Intermediate Similarity	NPC290194
0.8481	Intermediate Similarity	NPC125801
0.8481	Intermediate Similarity	NPC261271
0.8481	Intermediate Similarity	NPC475348
0.848	Intermediate Similarity	NPC477683
0.848	Intermediate Similarity	NPC477682
0.8476	Intermediate Similarity	NPC476506
0.8476	Intermediate Similarity	NPC470810
0.8466	Intermediate Similarity	NPC164110
0.8466	Intermediate Similarity	NPC246647
0.8466	Intermediate Similarity	NPC96342
0.8466	Intermediate Similarity	NPC282390
0.8466	Intermediate Similarity	NPC212967
0.8466	Intermediate Similarity	NPC281137
0.8466	Intermediate Similarity	NPC263483
0.8462	Intermediate Similarity	NPC477836
0.8462	Intermediate Similarity	NPC167663
0.8462	Intermediate Similarity	NPC293545
0.8462	Intermediate Similarity	NPC477529
0.8462	Intermediate Similarity	NPC174905
0.8457	Intermediate Similarity	NPC205026
0.8457	Intermediate Similarity	NPC52611
0.8457	Intermediate Similarity	NPC150908
0.8457	Intermediate Similarity	NPC55662
0.8457	Intermediate Similarity	NPC100049
0.8457	Intermediate Similarity	NPC186227
0.8457	Intermediate Similarity	NPC215203
0.8457	Intermediate Similarity	NPC121649
0.8457	Intermediate Similarity	NPC166054
0.8457	Intermediate Similarity	NPC158027
0.8457	Intermediate Similarity	NPC159707
0.8457	Intermediate Similarity	NPC248739
0.8457	Intermediate Similarity	NPC265624
0.8457	Intermediate Similarity	NPC14606
0.8452	Intermediate Similarity	NPC300307
0.8452	Intermediate Similarity	NPC473096
0.8452	Intermediate Similarity	NPC188079
0.8452	Intermediate Similarity	NPC473095
0.8448	Intermediate Similarity	NPC197972
0.8447	Intermediate Similarity	NPC175978
0.8447	Intermediate Similarity	NPC180944
0.8443	Intermediate Similarity	NPC120857
0.8443	Intermediate Similarity	NPC85047
0.8443	Intermediate Similarity	NPC251336
0.8443	Intermediate Similarity	NPC17274
0.8442	Intermediate Similarity	NPC243528
0.8442	Intermediate Similarity	NPC251681
0.8438	Intermediate Similarity	NPC325983

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 NPC219686 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	425
0.1-0.2	1061
0.2-0.3	1788
0.3-0.4	2794
0.4-0.5	1847
0.5-0.6	830
0.6-0.7	262
0.7-0.8	135
0.8-0.85	5
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8882	High Similarity	NPD6959	Discontinued
0.8554	High Similarity	NPD7473	Discontinued
0.8526	High Similarity	NPD7390	Discontinued
0.8485	Intermediate Similarity	NPD6232	Discontinued
0.8354	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD7819	Suspended
0.8059	Intermediate Similarity	NPD6166	Phase 2
0.8059	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD2532	Approved
0.8012	Intermediate Similarity	NPD2533	Approved
0.8012	Intermediate Similarity	NPD2534	Approved
0.8	Intermediate Similarity	NPD1607	Approved
0.7988	Intermediate Similarity	NPD4380	Phase 2
0.7975	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD7411	Suspended
0.7917	Intermediate Similarity	NPD7075	Discontinued
0.7898	Intermediate Similarity	NPD1510	Phase 2
0.7889	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD6651	Approved
0.7871	Intermediate Similarity	NPD1240	Approved
0.7816	Intermediate Similarity	NPD5844	Phase 1
0.7816	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD3749	Approved
0.7784	Intermediate Similarity	NPD6801	Discontinued
0.7751	Intermediate Similarity	NPD7768	Phase 2
0.7744	Intermediate Similarity	NPD1512	Approved
0.7738	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD3226	Approved
0.7702	Intermediate Similarity	NPD2800	Approved
0.7692	Intermediate Similarity	NPD3817	Phase 2
0.7688	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD1934	Approved
0.7667	Intermediate Similarity	NPD8150	Discontinued
0.7665	Intermediate Similarity	NPD6599	Discontinued
0.7654	Intermediate Similarity	NPD3750	Approved
0.7654	Intermediate Similarity	NPD7003	Approved
0.7647	Intermediate Similarity	NPD3882	Suspended
0.764	Intermediate Similarity	NPD1549	Phase 2
0.7633	Intermediate Similarity	NPD2801	Approved
0.7627	Intermediate Similarity	NPD6797	Phase 2
0.7625	Intermediate Similarity	NPD5408	Approved
0.7625	Intermediate Similarity	NPD2935	Discontinued
0.7625	Intermediate Similarity	NPD5406	Approved
0.7625	Intermediate Similarity	NPD6099	Approved
0.7625	Intermediate Similarity	NPD5405	Approved
0.7625	Intermediate Similarity	NPD6100	Approved
0.7625	Intermediate Similarity	NPD5404	Approved
0.7622	Intermediate Similarity	NPD1511	Approved
0.7584	Intermediate Similarity	NPD7251	Discontinued
0.7584	Intermediate Similarity	NPD6559	Discontinued
0.7576	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7808	Phase 3
0.7528	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2796	Approved
0.7515	Intermediate Similarity	NPD6799	Approved
0.7514	Intermediate Similarity	NPD5494	Approved
0.75	Intermediate Similarity	NPD6779	Approved
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD6777	Approved
0.75	Intermediate Similarity	NPD6776	Approved
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD6782	Approved
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7435	Discontinued
0.7472	Intermediate Similarity	NPD7074	Phase 3
0.7458	Intermediate Similarity	NPD3751	Discontinued
0.7439	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7870	Phase 2
0.7435	Intermediate Similarity	NPD7871	Phase 2
0.7429	Intermediate Similarity	NPD5710	Approved
0.7429	Intermediate Similarity	NPD5711	Approved
0.7427	Intermediate Similarity	NPD1465	Phase 2
0.7416	Intermediate Similarity	NPD7054	Approved
0.7403	Intermediate Similarity	NPD8313	Approved
0.7403	Intermediate Similarity	NPD8312	Approved
0.7396	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5402	Approved
0.7382	Intermediate Similarity	NPD7697	Approved
0.7382	Intermediate Similarity	NPD7698	Approved
0.7382	Intermediate Similarity	NPD7696	Phase 3
0.7378	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7472	Approved
0.7371	Intermediate Similarity	NPD8151	Discontinued
0.7362	Intermediate Similarity	NPD2346	Discontinued
0.7348	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD3748	Approved
0.7342	Intermediate Similarity	NPD4625	Phase 3
0.733	Intermediate Similarity	NPD3787	Discontinued
0.7296	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7458	Discontinued
0.7288	Intermediate Similarity	NPD3926	Phase 2
0.7278	Intermediate Similarity	NPD5403	Approved
0.7273	Intermediate Similarity	NPD1201	Approved
0.7267	Intermediate Similarity	NPD37	Approved
0.7263	Intermediate Similarity	NPD3818	Discontinued
0.7262	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD3300	Phase 2
0.7245	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7874	Approved
0.7239	Intermediate Similarity	NPD2799	Discontinued
0.7239	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6535	Approved
0.7234	Intermediate Similarity	NPD6534	Approved
0.7232	Intermediate Similarity	NPD7229	Phase 3
0.7231	Intermediate Similarity	NPD7701	Phase 2
0.7228	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7801	Approved
0.7197	Intermediate Similarity	NPD1470	Approved
0.7195	Intermediate Similarity	NPD1551	Phase 2
0.7191	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD920	Approved
0.7176	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD1247	Approved
0.717	Intermediate Similarity	NPD4908	Phase 1
0.7169	Intermediate Similarity	NPD1243	Approved
0.7165	Intermediate Similarity	NPD8320	Phase 1
0.7165	Intermediate Similarity	NPD8319	Approved
0.716	Intermediate Similarity	NPD5401	Approved
0.7159	Intermediate Similarity	NPD919	Approved
0.7159	Intermediate Similarity	NPD6234	Discontinued
0.7158	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2344	Approved
0.7143	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD4965	Approved
0.7143	Intermediate Similarity	NPD4967	Phase 2
0.7134	Intermediate Similarity	NPD1283	Approved
0.7126	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7783	Phase 2
0.712	Intermediate Similarity	NPD7700	Phase 2
0.712	Intermediate Similarity	NPD7699	Phase 2
0.7099	Intermediate Similarity	NPD943	Approved
0.7078	Intermediate Similarity	NPD1651	Approved
0.7072	Intermediate Similarity	NPD7177	Discontinued
0.7072	Intermediate Similarity	NPD7228	Approved
0.707	Intermediate Similarity	NPD4749	Approved
0.7068	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6823	Phase 2
0.7056	Intermediate Similarity	NPD2403	Approved
0.7049	Intermediate Similarity	NPD5953	Discontinued
0.7044	Intermediate Similarity	NPD2798	Approved
0.7033	Intermediate Similarity	NPD7286	Phase 2
0.7005	Intermediate Similarity	NPD8434	Phase 2
0.6983	Remote Similarity	NPD7199	Phase 2
0.6982	Remote Similarity	NPD2309	Approved
0.6976	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD3764	Approved
0.6975	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4360	Phase 2
0.6963	Remote Similarity	NPD4363	Phase 3
0.6959	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD1471	Phase 3
0.6943	Remote Similarity	NPD1281	Approved
0.6941	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD4287	Approved
0.6928	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4628	Phase 3
0.6899	Remote Similarity	NPD3972	Approved
0.689	Remote Similarity	NPD4060	Phase 1
0.689	Remote Similarity	NPD2979	Phase 3
0.6872	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2313	Discontinued
0.6869	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2654	Approved
0.6821	Remote Similarity	NPD6273	Approved
0.6815	Remote Similarity	NPD4626	Approved
0.6802	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD4288	Approved
0.6786	Remote Similarity	NPD2438	Suspended
0.6784	Remote Similarity	NPD6190	Approved
0.6778	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7654	Discontinued
0.6768	Remote Similarity	NPD3268	Approved
0.6753	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4361	Phase 2
0.675	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD230	Phase 1
0.6742	Remote Similarity	NPD8455	Phase 2
0.6742	Remote Similarity	NPD5761	Phase 2
0.6742	Remote Similarity	NPD5760	Phase 2
0.674	Remote Similarity	NPD6746	Phase 2
0.6738	Remote Similarity	NPD7240	Approved
0.6736	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6212	Phase 3
0.6736	Remote Similarity	NPD6213	Phase 3
0.673	Remote Similarity	NPD1610	Phase 2
0.6726	Remote Similarity	NPD4308	Phase 3
0.6708	Remote Similarity	NPD1876	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