NPASS Compound

Structure

NPC272174 OpenBabel07101719132D 34 40 0 0 1 0 0 0 0 0999 V2000 -5.1377 -0.8695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7550 -1.7934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1641 3.3088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1518 3.1524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5348 2.5317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5102 2.2188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4392 -1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4392 -1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4392 0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8931 1.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4392 0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4899 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8808 1.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4899 0.8090 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 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1463 -0.0000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1463 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0373 0.4540 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 1.1180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1266 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 26 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 15 2 0 0 0 0 8 17 2 0 0 0 0 9 18 2 0 0 0 0 10 19 2 0 0 0 0 11 12 2 0 0 0 0 11 26 1 0 0 0 0 12 30 1 0 0 0 0 13 16 1 0 0 0 0 13 20 2 0 0 0 0 14 27 1 0 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 16 22 2 0 0 0 0 17 19 1 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 20 24 1 0 0 0 0 20 30 1 0 0 0 0 21 14 1 6 0 0 0 21 23 1 0 0 0 0 21 31 1 0 0 0 0 22 26 1 0 0 0 0 22 28 1 0 0 0 0 23 30 1 0 0 0 0 23 32 2 0 0 0 0 24 31 1 0 0 0 0 24 33 2 0 0 0 0 25 27 1 6 0 0 0 25 29 1 0 0 0 0 25 31 1 0 0 0 0 27 34 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.18
Volume:	457.01
LogP:	4.272
LogD:	3.564
LogS:	-5.316
# Rotatable Bonds:	0
TPSA:	88.67
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.488
Synthetic Accessibility Score:	4.598
Fsp3:	0.259
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.37
MDCK Permeability:	2.415006747469306e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.715
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.177
30% Bioavailability (F30%):	0.19

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.186
Plasma Protein Binding (PPB):	96.54003143310547%
Volume Distribution (VD):	0.754
Pgp-substrate:	1.184562087059021%

ADMET: Metabolism

CYP1A2-inhibitor:	0.223
CYP1A2-substrate:	0.2
CYP2C19-inhibitor:	0.932
CYP2C19-substrate:	0.53
CYP2C9-inhibitor:	0.936
CYP2C9-substrate:	0.926
CYP2D6-inhibitor:	0.445
CYP2D6-substrate:	0.149
CYP3A4-inhibitor:	0.951
CYP3A4-substrate:	0.873

ADMET: Excretion

Clearance (CL):	2.898
Half-life (T1/2):	0.183

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.933
Drug-inuced Liver Injury (DILI):	0.989
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.896
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.84
Carcinogencity:	0.892
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC272174

Natural Product ID:	NPC272174
*Common Name:**	Okaramine I
IUPAC Name:	n.a.
Synonyms:	Okaramine I
Standard InCHIKey:	CTRNZLRKISVIAG-LBJKZLEUSA-N
Standard InCHI:	InChI=1S/C27H24N4O3/c1-26(2)11-12-30-20(13-16-15-7-3-5-9-18(15)28-22(16)26)24(33)31-21(23(30)32)14-27(34)17-8-4-6-10-19(17)29-25(27)31/h3-13,21,25,28-29,34H,14H2,1-2H3/b12-11-,20-13-/t21-,25+,27-/m1/s1
SMILES:	CC1(C)C=CN2C(=Cc3c4ccccc4[nH]c13)C(=O)N1[C@H](C[C@]3(c4ccccc4N[C@@H]13)O)C2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454564
PubChem CID:	10575622
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001733] Pyrroloindoles

*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
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075772]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16155971]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19824618]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21667999]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	latex	n.a.	PMID[21854017]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[324959]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO8911	Aspergillus aculeatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
LD50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3978	Organism	Bombyx mori	Bombyx mori	LD50	>	100.0	ug	PMID[522304]

☑ 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 NPC272174 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	399
0.1-0.2	2191
0.2-0.3	12566
0.3-0.4	18705
0.4-0.5	3706
0.5-0.6	2716
0.6-0.7	1942
0.7-0.8	456
0.8-0.85	12
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9848	High Similarity	NPC474896
0.9798	High Similarity	NPC31097
0.8694	High Similarity	NPC14812
0.8387	Intermediate Similarity	NPC477177
0.8341	Intermediate Similarity	NPC470729
0.8341	Intermediate Similarity	NPC477175
0.8341	Intermediate Similarity	NPC470730
0.8341	Intermediate Similarity	NPC477176
0.8303	Intermediate Similarity	NPC475969
0.8303	Intermediate Similarity	NPC474877
0.8303	Intermediate Similarity	NPC475859
0.8265	Intermediate Similarity	NPC165743
0.8227	Intermediate Similarity	NPC63279
0.819	Intermediate Similarity	NPC297642
0.8122	Intermediate Similarity	NPC470732
0.8122	Intermediate Similarity	NPC470731
0.7933	Intermediate Similarity	NPC471944
0.7757	Intermediate Similarity	NPC162860
0.775	Intermediate Similarity	NPC91179
0.7746	Intermediate Similarity	NPC54420
0.7734	Intermediate Similarity	NPC94752
0.7709	Intermediate Similarity	NPC325976
0.7703	Intermediate Similarity	NPC476817
0.7703	Intermediate Similarity	NPC171317
0.7677	Intermediate Similarity	NPC161861
0.7636	Intermediate Similarity	NPC477714
0.7635	Intermediate Similarity	NPC472294
0.7626	Intermediate Similarity	NPC322064
0.7611	Intermediate Similarity	NPC326363
0.761	Intermediate Similarity	NPC17059
0.76	Intermediate Similarity	NPC476491
0.7591	Intermediate Similarity	NPC477715
0.7586	Intermediate Similarity	NPC470205
0.758	Intermediate Similarity	NPC478157
0.757	Intermediate Similarity	NPC473376
0.7561	Intermediate Similarity	NPC141612
0.7561	Intermediate Similarity	NPC17273
0.7561	Intermediate Similarity	NPC135601
0.7549	Intermediate Similarity	NPC228835
0.7536	Intermediate Similarity	NPC131887
0.7523	Intermediate Similarity	NPC82370
0.7512	Intermediate Similarity	NPC300183
0.7512	Intermediate Similarity	NPC478158
0.7512	Intermediate Similarity	NPC133003
0.75	Intermediate Similarity	NPC477979
0.75	Intermediate Similarity	NPC312942
0.75	Intermediate Similarity	NPC327095
0.75	Intermediate Similarity	NPC270918
0.7488	Intermediate Similarity	NPC213629
0.7477	Intermediate Similarity	NPC471436
0.7467	Intermediate Similarity	NPC229893
0.7467	Intermediate Similarity	NPC40455
0.7465	Intermediate Similarity	NPC71238
0.7443	Intermediate Similarity	NPC54981
0.7442	Intermediate Similarity	NPC476098
0.7441	Intermediate Similarity	NPC470787
0.7441	Intermediate Similarity	NPC472539
0.7441	Intermediate Similarity	NPC472540
0.7438	Intermediate Similarity	NPC11126
0.7438	Intermediate Similarity	NPC219336
0.7434	Intermediate Similarity	NPC19170
0.7432	Intermediate Similarity	NPC472285
0.7419	Intermediate Similarity	NPC471155
0.7418	Intermediate Similarity	NPC293917
0.7412	Intermediate Similarity	NPC56109
0.7412	Intermediate Similarity	NPC191382
0.7406	Intermediate Similarity	NPC141454
0.7406	Intermediate Similarity	NPC472542
0.7406	Intermediate Similarity	NPC472541
0.7399	Intermediate Similarity	NPC475736
0.7399	Intermediate Similarity	NPC303658
0.7399	Intermediate Similarity	NPC281049
0.7399	Intermediate Similarity	NPC473310
0.7389	Intermediate Similarity	NPC15573
0.7389	Intermediate Similarity	NPC183662
0.7389	Intermediate Similarity	NPC217372
0.7385	Intermediate Similarity	NPC270241
0.7382	Intermediate Similarity	NPC470784
0.738	Intermediate Similarity	NPC69843
0.7376	Intermediate Similarity	NPC54744
0.7373	Intermediate Similarity	NPC225400
0.7373	Intermediate Similarity	NPC277350
0.7368	Intermediate Similarity	NPC324091
0.7361	Intermediate Similarity	NPC317701
0.7361	Intermediate Similarity	NPC165599
0.7354	Intermediate Similarity	NPC305984
0.7352	Intermediate Similarity	NPC107077
0.7352	Intermediate Similarity	NPC223791
0.7345	Intermediate Similarity	NPC155444
0.7339	Intermediate Similarity	NPC28945
0.7339	Intermediate Similarity	NPC472538
0.7339	Intermediate Similarity	NPC184225
0.7339	Intermediate Similarity	NPC470786
0.7336	Intermediate Similarity	NPC297862
0.7336	Intermediate Similarity	NPC33949
0.7336	Intermediate Similarity	NPC194740
0.733	Intermediate Similarity	NPC471194
0.733	Intermediate Similarity	NPC471193
0.733	Intermediate Similarity	NPC75634
0.733	Intermediate Similarity	NPC153980
0.733	Intermediate Similarity	NPC6865
0.7325	Intermediate Similarity	NPC24370
0.7325	Intermediate Similarity	NPC319232
0.7324	Intermediate Similarity	NPC232130
0.7321	Intermediate Similarity	NPC321708
0.7317	Intermediate Similarity	NPC16659
0.7316	Intermediate Similarity	NPC89987
0.7308	Intermediate Similarity	NPC470785
0.7303	Intermediate Similarity	NPC314882
0.7302	Intermediate Similarity	NPC214428
0.7302	Intermediate Similarity	NPC252338
0.7288	Intermediate Similarity	NPC295452
0.7288	Intermediate Similarity	NPC171393
0.7285	Intermediate Similarity	NPC320968
0.7285	Intermediate Similarity	NPC72956
0.7269	Intermediate Similarity	NPC475506
0.7268	Intermediate Similarity	NPC265710
0.7265	Intermediate Similarity	NPC184680
0.726	Intermediate Similarity	NPC473362
0.726	Intermediate Similarity	NPC166492
0.726	Intermediate Similarity	NPC244741
0.7259	Intermediate Similarity	NPC299594
0.7244	Intermediate Similarity	NPC264285
0.7243	Intermediate Similarity	NPC227582
0.7238	Intermediate Similarity	NPC221873
0.7237	Intermediate Similarity	NPC64216
0.7235	Intermediate Similarity	NPC155143
0.7233	Intermediate Similarity	NPC469896
0.7232	Intermediate Similarity	NPC36405
0.7225	Intermediate Similarity	NPC478077
0.7222	Intermediate Similarity	NPC471122
0.722	Intermediate Similarity	NPC473380
0.722	Intermediate Similarity	NPC240088
0.7215	Intermediate Similarity	NPC471191
0.721	Intermediate Similarity	NPC220852
0.721	Intermediate Similarity	NPC284888
0.7209	Intermediate Similarity	NPC473640
0.7205	Intermediate Similarity	NPC476818
0.7202	Intermediate Similarity	NPC98715
0.72	Intermediate Similarity	NPC476118
0.72	Intermediate Similarity	NPC312645
0.7193	Intermediate Similarity	NPC220851
0.7191	Intermediate Similarity	NPC285343
0.719	Intermediate Similarity	NPC153400
0.7184	Intermediate Similarity	NPC478006
0.7182	Intermediate Similarity	NPC243850
0.7181	Intermediate Similarity	NPC474195
0.7181	Intermediate Similarity	NPC323969
0.7177	Intermediate Similarity	NPC99939
0.7177	Intermediate Similarity	NPC15102
0.7177	Intermediate Similarity	NPC308931
0.7176	Intermediate Similarity	NPC100321
0.7174	Intermediate Similarity	NPC909
0.7174	Intermediate Similarity	NPC475338
0.7174	Intermediate Similarity	NPC214142
0.717	Intermediate Similarity	NPC476460
0.7167	Intermediate Similarity	NPC63031
0.7164	Intermediate Similarity	NPC471124
0.7162	Intermediate Similarity	NPC234999
0.7162	Intermediate Similarity	NPC475422
0.7161	Intermediate Similarity	NPC41679
0.7156	Intermediate Similarity	NPC471192
0.7156	Intermediate Similarity	NPC469928
0.715	Intermediate Similarity	NPC157828
0.715	Intermediate Similarity	NPC195239
0.7149	Intermediate Similarity	NPC315467
0.7143	Intermediate Similarity	NPC34580
0.7143	Intermediate Similarity	NPC118559
0.7143	Intermediate Similarity	NPC475258
0.7143	Intermediate Similarity	NPC31700
0.7143	Intermediate Similarity	NPC261251
0.7143	Intermediate Similarity	NPC304307
0.7143	Intermediate Similarity	NPC17487
0.7143	Intermediate Similarity	NPC124920
0.7143	Intermediate Similarity	NPC89508
0.7143	Intermediate Similarity	NPC201831
0.7143	Intermediate Similarity	NPC282247
0.7137	Intermediate Similarity	NPC323752
0.7136	Intermediate Similarity	NPC471386
0.713	Intermediate Similarity	NPC474196
0.713	Intermediate Similarity	NPC265576
0.7124	Intermediate Similarity	NPC27041
0.7123	Intermediate Similarity	NPC472112
0.7123	Intermediate Similarity	NPC329858
0.7123	Intermediate Similarity	NPC295548
0.712	Intermediate Similarity	NPC478010
0.712	Intermediate Similarity	NPC478009
0.7119	Intermediate Similarity	NPC15801
0.7118	Intermediate Similarity	NPC16352
0.7118	Intermediate Similarity	NPC253987
0.7117	Intermediate Similarity	NPC476116
0.7116	Intermediate Similarity	NPC11445
0.7115	Intermediate Similarity	NPC321939
0.7114	Intermediate Similarity	NPC271797
0.7114	Intermediate Similarity	NPC21174
0.7114	Intermediate Similarity	NPC271734
0.7113	Intermediate Similarity	NPC477107
0.7113	Intermediate Similarity	NPC477108
0.7113	Intermediate Similarity	NPC477109
0.7112	Intermediate Similarity	NPC100547

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 NPC272174 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	514
0.2-0.3	788
0.3-0.4	1569
0.4-0.5	2424
0.5-0.6	2448
0.6-0.7	1086
0.7-0.8	104
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.783	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7783	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD8094	Discontinued
0.7692	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD8093	Discontinued
0.765	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7619	Phase 3
0.7644	Intermediate Similarity	NPD7618	Phase 3
0.7634	Intermediate Similarity	NPD7603	Discontinued
0.7604	Intermediate Similarity	NPD7470	Discontinued
0.7557	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD6165	Phase 2
0.7522	Intermediate Similarity	NPD6164	Phase 2
0.75	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8322	Phase 2
0.743	Intermediate Similarity	NPD7817	Phase 1
0.7418	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD6999	Discontinued
0.7412	Intermediate Similarity	NPD7780	Approved
0.7412	Intermediate Similarity	NPD7781	Approved
0.7407	Intermediate Similarity	NPD5426	Phase 3
0.7397	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7666	Phase 3
0.7385	Intermediate Similarity	NPD6376	Discontinued
0.7385	Intermediate Similarity	NPD7665	Phase 2
0.738	Intermediate Similarity	NPD7824	Approved
0.7376	Intermediate Similarity	NPD5065	Approved
0.7359	Intermediate Similarity	NPD7950	Approved
0.7359	Intermediate Similarity	NPD7952	Approved
0.7359	Intermediate Similarity	NPD7789	Approved
0.7359	Intermediate Similarity	NPD7953	Approved
0.7359	Intermediate Similarity	NPD7790	Approved
0.7359	Intermediate Similarity	NPD7791	Approved
0.7359	Intermediate Similarity	NPD7951	Approved
0.7349	Intermediate Similarity	NPD7727	Phase 2
0.7349	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD8115	Approved
0.7327	Intermediate Similarity	NPD8114	Approved
0.7321	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD2510	Approved
0.7306	Intermediate Similarity	NPD2509	Approved
0.7294	Intermediate Similarity	NPD7001	Phase 3
0.7293	Intermediate Similarity	NPD7731	Approved
0.7293	Intermediate Similarity	NPD7730	Approved
0.7281	Intermediate Similarity	NPD7271	Approved
0.7265	Intermediate Similarity	NPD7970	Approved
0.7265	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD8289	Discontinued
0.7248	Intermediate Similarity	NPD5901	Discontinued
0.724	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6176	Phase 1
0.72	Intermediate Similarity	NPD2813	Phase 3
0.72	Intermediate Similarity	NPD5140	Approved
0.72	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5138	Approved
0.72	Intermediate Similarity	NPD2812	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7717	Approved
0.7162	Intermediate Similarity	NPD7716	Approved
0.715	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6724	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD3757	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6248	Phase 2
0.7097	Intermediate Similarity	NPD6249	Phase 2
0.7091	Intermediate Similarity	NPD8098	Approved
0.7089	Intermediate Similarity	NPD8240	Discontinued
0.7083	Intermediate Similarity	NPD5003	Discontinued
0.7081	Intermediate Similarity	NPD5596	Phase 2
0.7072	Intermediate Similarity	NPD2442	Approved
0.7072	Intermediate Similarity	NPD2916	Discontinued
0.7072	Intermediate Similarity	NPD2443	Approved
0.7067	Intermediate Similarity	NPD3243	Approved
0.7056	Intermediate Similarity	NPD2882	Phase 1
0.7056	Intermediate Similarity	NPD6665	Discontinued
0.7043	Intermediate Similarity	NPD6995	Phase 1
0.7042	Intermediate Similarity	NPD4499	Approved
0.7028	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD7711	Discontinued
0.7022	Intermediate Similarity	NPD3917	Approved
0.7022	Intermediate Similarity	NPD8097	Phase 3
0.7022	Intermediate Similarity	NPD3916	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD8096	Phase 3
0.7022	Intermediate Similarity	NPD3918	Approved
0.7021	Intermediate Similarity	NPD4885	Approved
0.7014	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6557	Phase 2
0.7013	Intermediate Similarity	NPD6752	Phase 1
0.7013	Intermediate Similarity	NPD7202	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6753	Phase 1
0.7009	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6664	Approved
0.7005	Intermediate Similarity	NPD2880	Discontinued
0.7004	Intermediate Similarity	NPD3394	Approved
0.7004	Intermediate Similarity	NPD3393	Approved
0.7004	Intermediate Similarity	NPD3389	Approved
0.7	Intermediate Similarity	NPD2094	Phase 2
0.7	Intermediate Similarity	NPD2095	Phase 2
0.7	Intermediate Similarity	NPD2092	Phase 2
0.6996	Remote Similarity	NPD4558	Phase 2
0.6995	Remote Similarity	NPD4334	Discontinued
0.6992	Remote Similarity	NPD7415	Suspended
0.6991	Remote Similarity	NPD4602	Approved
0.6991	Remote Similarity	NPD7944	Discontinued
0.6987	Remote Similarity	NPD7168	Phase 3
0.6986	Remote Similarity	NPD484	Approved
0.6986	Remote Similarity	NPD6595	Phase 3
0.6982	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6403	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7568	Phase 1
0.6981	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3915	Approved
0.6976	Remote Similarity	NPD1325	Approved
0.6976	Remote Similarity	NPD1326	Approved
0.6972	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5487	Phase 1
0.6967	Remote Similarity	NPD2096	Phase 2
0.6967	Remote Similarity	NPD2091	Phase 2
0.6958	Remote Similarity	NPD8349	Phase 1
0.6957	Remote Similarity	NPD482	Approved
0.6955	Remote Similarity	NPD5017	Discontinued
0.6952	Remote Similarity	NPD3178	Discontinued
0.6948	Remote Similarity	NPD4948	Discontinued
0.6947	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7308	Discontinued
0.6937	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.693	Remote Similarity	NPD7543	Phase 2
0.6927	Remote Similarity	NPD2844	Phase 3
0.6923	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5807	Phase 2
0.6913	Remote Similarity	NPD5199	Approved
0.6913	Remote Similarity	NPD5198	Approved
0.6912	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4500	Approved
0.6909	Remote Similarity	NPD4601	Approved
0.6909	Remote Similarity	NPD4501	Approved
0.6909	Remote Similarity	NPD4600	Approved
0.6907	Remote Similarity	NPD7688	Phase 1
0.6906	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6452	Discontinued
0.6889	Remote Similarity	NPD2408	Discontinued
0.6884	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD6158	Phase 2
0.6884	Remote Similarity	NPD1043	Phase 3
0.6878	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6492	Phase 2
0.6872	Remote Similarity	NPD7921	Approved
0.6869	Remote Similarity	NPD3961	Discontinued
0.6861	Remote Similarity	NPD8272	Phase 2
0.6857	Remote Similarity	NPD8386	Phase 2
0.6852	Remote Similarity	NPD6022	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7948	Phase 1
0.6842	Remote Similarity	NPD2380	Approved
0.6842	Remote Similarity	NPD2381	Approved
0.6842	Remote Similarity	NPD2382	Approved
0.684	Remote Similarity	NPD3318	Approved
0.684	Remote Similarity	NPD3319	Phase 1
0.684	Remote Similarity	NPD3320	Approved
0.6838	Remote Similarity	NPD7269	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD4462	Approved
0.6834	Remote Similarity	NPD4463	Approved
0.6828	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD750	Phase 2
0.6826	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD5473	Discontinued
0.6822	Remote Similarity	NPD7026	Phase 2
0.6822	Remote Similarity	NPD5809	Phase 3
0.6822	Remote Similarity	NPD3315	Phase 3
0.682	Remote Similarity	NPD4315	Phase 2
0.681	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD1096	Discontinued
0.6806	Remote Similarity	NPD3439	Approved
0.6802	Remote Similarity	NPD5552	Discontinued
0.6798	Remote Similarity	NPD4852	Phase 2
0.6792	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.679	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD3814	Phase 1
0.6787	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD8282	Approved
0.6786	Remote Similarity	NPD8283	Approved
0.6786	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD56	Approved
0.6784	Remote Similarity	NPD7825	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