NPASS Compound

Structure

CID328318 OpenBabel06191716202D 28 31 0 0 1 0 0 0 0 0999 V2000 -2.8254 5.3486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4179 4.5465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0321 1.4037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0321 2.3323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2279 0.9394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2279 2.7966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6100 -0.0026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8048 -0.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4270 6.1665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8138 2.3288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4825 4.5517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8901 5.3538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4237 1.4037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6157 0.9358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0050 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4237 2.3323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8188 1.4027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0103 3.7444 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.4917 6.1718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8110 1.4015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8046 2.3406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0092 0.9343 0.0000 C 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 -0.0194 5.3644 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6190 2.7979 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6286 0.9385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9250 3.7496 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0286 6.9844 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 13 2 0 0 0 0 6 16 2 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 23 1 0 0 0 0 9 12 2 0 0 0 0 9 19 1 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 11 24 1 0 0 0 0 13 14 1 0 0 0 0 13 16 1 0 0 0 0 14 20 2 0 0 0 0 15 18 1 0 0 0 0 15 21 1 0 0 0 0 16 25 1 0 0 0 0 17 22 1 0 0 0 0 17 26 2 0 0 0 0 18 27 1 0 0 0 0 19 24 2 3 0 0 0 19 28 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 25 2 0 0 0 0 22 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	373.14
Volume:	385.202
LogP:	4.02
LogD:	3.073
LogS:	-4.714
# Rotatable Bonds:	4
TPSA:	95.67
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.324
Synthetic Accessibility Score:	3.281
Fsp3:	0.182
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.852
MDCK Permeability:	1.291968237637775e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.136
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	96.93399810791016%
Volume Distribution (VD):	0.63
Pgp-substrate:	1.684362769126892%

ADMET: Metabolism

CYP1A2-inhibitor:	0.903
CYP1A2-substrate:	0.202
CYP2C19-inhibitor:	0.221
CYP2C19-substrate:	0.093
CYP2C9-inhibitor:	0.749
CYP2C9-substrate:	0.727
CYP2D6-inhibitor:	0.659
CYP2D6-substrate:	0.202
CYP3A4-inhibitor:	0.158
CYP3A4-substrate:	0.12

ADMET: Excretion

Clearance (CL):	0.848
Half-life (T1/2):	0.253

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.563
Drug-inuced Liver Injury (DILI):	0.986
AMES Toxicity:	0.812
Rat Oral Acute Toxicity:	0.056
Maximum Recommended Daily Dose:	0.623
Skin Sensitization:	0.925
Carcinogencity:	0.458
Eye Corrosion:	0.004
Eye Irritation:	0.146
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC328318

Natural Product ID:	NPC328318
*Common Name:**	Cystodytin D
IUPAC Name:	n.a.
Synonyms:	Cystodytin D
Standard InCHIKey:	ANJZOYDQOAVRCX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C22H19N3O3/c1-12(2)9-19(28)24-11-18(27)15-10-17(26)22-20-14(7-8-23-22)13-5-3-4-6-16(13)25-21(15)20/h3-10,18,27H,11H2,1-2H3,(H,24,28)
SMILES:	CC(=CC(=O)NCC(C1=CC(=O)C2=NC=CC3=C2C1=NC4=CC=CC=C34)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489143
PubChem CID:	23427217
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000274] Acridines [CHEMONTID:0001763] Pyridoacridines [CHEMONTID:0001810] Pyridoacridones [CHEMONTID:0002826] Pyrido[2,3,4-kl]acridones

*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
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1812214]
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20491501]
NPO9248	Cystodytes dellechiajei	Species	Polycitoridae	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
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	=	1.1	ug.mL-1	PMID[449421]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1.4	ug.mL-1	PMID[449421]

☑ 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 NPC328318 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	296
0.1-0.2	1652
0.2-0.3	9809
0.3-0.4	15979
0.4-0.5	10062
0.5-0.6	2070
0.6-0.7	2336
0.7-0.8	478
0.8-0.85	8
0.85-0.9	1
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC328596
0.9727	High Similarity	NPC317373
0.9672	High Similarity	NPC327592
0.9368	High Similarity	NPC317752
0.9316	High Similarity	NPC318299
0.8827	High Similarity	NPC157583
0.8636	High Similarity	NPC237740
0.8503	High Similarity	NPC255909
0.8396	Intermediate Similarity	NPC118084
0.8289	Intermediate Similarity	NPC207851
0.8232	Intermediate Similarity	NPC472064
0.8118	Intermediate Similarity	NPC237188
0.8115	Intermediate Similarity	NPC103119
0.805	Intermediate Similarity	NPC472065
0.8038	Intermediate Similarity	NPC322482
0.801	Intermediate Similarity	NPC106824
0.799	Intermediate Similarity	NPC472062
0.799	Intermediate Similarity	NPC472063
0.799	Intermediate Similarity	NPC472069
0.799	Intermediate Similarity	NPC57398
0.7929	Intermediate Similarity	NPC284338
0.7914	Intermediate Similarity	NPC139763
0.7872	Intermediate Similarity	NPC203754
0.7872	Intermediate Similarity	NPC150048
0.7843	Intermediate Similarity	NPC472070
0.7839	Intermediate Similarity	NPC123395
0.782	Intermediate Similarity	NPC216612
0.7806	Intermediate Similarity	NPC216550
0.7751	Intermediate Similarity	NPC472285
0.7749	Intermediate Similarity	NPC15840
0.7677	Intermediate Similarity	NPC267343
0.7662	Intermediate Similarity	NPC81535
0.7656	Intermediate Similarity	NPC471997
0.765	Intermediate Similarity	NPC227582
0.7647	Intermediate Similarity	NPC41717
0.7617	Intermediate Similarity	NPC229893
0.7614	Intermediate Similarity	NPC154339
0.7612	Intermediate Similarity	NPC474916
0.7612	Intermediate Similarity	NPC34837
0.7598	Intermediate Similarity	NPC165599
0.7591	Intermediate Similarity	NPC477549
0.7583	Intermediate Similarity	NPC469727
0.7577	Intermediate Similarity	NPC159125
0.7552	Intermediate Similarity	NPC326575
0.7547	Intermediate Similarity	NPC473310
0.7537	Intermediate Similarity	NPC252338
0.7525	Intermediate Similarity	NPC149708
0.7513	Intermediate Similarity	NPC472323
0.7512	Intermediate Similarity	NPC98715
0.7512	Intermediate Similarity	NPC82370
0.7512	Intermediate Similarity	NPC472116
0.7512	Intermediate Similarity	NPC128244
0.75	Intermediate Similarity	NPC84347
0.7489	Intermediate Similarity	NPC477112
0.7488	Intermediate Similarity	NPC474767
0.7487	Intermediate Similarity	NPC117244
0.7487	Intermediate Similarity	NPC473763
0.7476	Intermediate Similarity	NPC118940
0.7475	Intermediate Similarity	NPC167710
0.7464	Intermediate Similarity	NPC470020
0.7464	Intermediate Similarity	NPC309845
0.7453	Intermediate Similarity	NPC477110
0.7452	Intermediate Similarity	NPC127677
0.7452	Intermediate Similarity	NPC258062
0.7449	Intermediate Similarity	NPC467063
0.7449	Intermediate Similarity	NPC258480
0.744	Intermediate Similarity	NPC238457
0.7438	Intermediate Similarity	NPC131887
0.7437	Intermediate Similarity	NPC95783
0.7433	Intermediate Similarity	NPC322644
0.7416	Intermediate Similarity	NPC271862
0.7415	Intermediate Similarity	NPC300183
0.7404	Intermediate Similarity	NPC46225
0.7404	Intermediate Similarity	NPC244741
0.7404	Intermediate Similarity	NPC225821
0.7402	Intermediate Similarity	NPC74413
0.7393	Intermediate Similarity	NPC87856
0.7393	Intermediate Similarity	NPC151976
0.7391	Intermediate Similarity	NPC314648
0.7391	Intermediate Similarity	NPC472259
0.7381	Intermediate Similarity	NPC123839
0.7379	Intermediate Similarity	NPC260900
0.7374	Intermediate Similarity	NPC66210
0.7371	Intermediate Similarity	NPC132211
0.7368	Intermediate Similarity	NPC266249
0.7358	Intermediate Similarity	NPC267965
0.7354	Intermediate Similarity	NPC97367
0.735	Intermediate Similarity	NPC83111
0.7339	Intermediate Similarity	NPC476818
0.7336	Intermediate Similarity	NPC312645
0.7336	Intermediate Similarity	NPC27041
0.7333	Intermediate Similarity	NPC133261
0.7333	Intermediate Similarity	NPC248462
0.733	Intermediate Similarity	NPC70949
0.7323	Intermediate Similarity	NPC472107
0.7323	Intermediate Similarity	NPC62510
0.7323	Intermediate Similarity	NPC79062
0.732	Intermediate Similarity	NPC24594
0.732	Intermediate Similarity	NPC472122
0.7306	Intermediate Similarity	NPC470018
0.7304	Intermediate Similarity	NPC141454
0.7304	Intermediate Similarity	NPC90229
0.7297	Intermediate Similarity	NPC207686
0.7295	Intermediate Similarity	NPC476874
0.729	Intermediate Similarity	NPC203614
0.729	Intermediate Similarity	NPC204491
0.729	Intermediate Similarity	NPC36405
0.7286	Intermediate Similarity	NPC477111
0.7286	Intermediate Similarity	NPC315555
0.7286	Intermediate Similarity	NPC90415
0.7277	Intermediate Similarity	NPC89508
0.7273	Intermediate Similarity	NPC284559
0.7273	Intermediate Similarity	NPC74575
0.7273	Intermediate Similarity	NPC476491
0.7273	Intermediate Similarity	NPC175602
0.7268	Intermediate Similarity	NPC212213
0.7265	Intermediate Similarity	NPC70155
0.7259	Intermediate Similarity	NPC191415
0.7259	Intermediate Similarity	NPC113626
0.7254	Intermediate Similarity	NPC158129
0.7251	Intermediate Similarity	NPC61038
0.725	Intermediate Similarity	NPC278434
0.7245	Intermediate Similarity	NPC248041
0.7245	Intermediate Similarity	NPC126709
0.7241	Intermediate Similarity	NPC474177
0.7238	Intermediate Similarity	NPC314297
0.7238	Intermediate Similarity	NPC193238
0.7238	Intermediate Similarity	NPC315545
0.7236	Intermediate Similarity	NPC282103
0.7233	Intermediate Similarity	NPC103361
0.7231	Intermediate Similarity	NPC267885
0.723	Intermediate Similarity	NPC219087
0.723	Intermediate Similarity	NPC110182
0.7228	Intermediate Similarity	NPC114974
0.7225	Intermediate Similarity	NPC477043
0.7222	Intermediate Similarity	NPC143533
0.7222	Intermediate Similarity	NPC48938
0.722	Intermediate Similarity	NPC49547
0.7215	Intermediate Similarity	NPC122436
0.7214	Intermediate Similarity	NPC321708
0.7214	Intermediate Similarity	NPC183805
0.7212	Intermediate Similarity	NPC41679
0.7208	Intermediate Similarity	NPC472105
0.7208	Intermediate Similarity	NPC24864
0.7208	Intermediate Similarity	NPC187827
0.7207	Intermediate Similarity	NPC477175
0.7207	Intermediate Similarity	NPC470730
0.7206	Intermediate Similarity	NPC135950
0.7206	Intermediate Similarity	NPC133366
0.7205	Intermediate Similarity	NPC208522
0.72	Intermediate Similarity	NPC478077
0.72	Intermediate Similarity	NPC62749
0.72	Intermediate Similarity	NPC235684
0.7196	Intermediate Similarity	NPC234078
0.7196	Intermediate Similarity	NPC236668
0.7196	Intermediate Similarity	NPC80681
0.7196	Intermediate Similarity	NPC221100
0.7194	Intermediate Similarity	NPC64436
0.7194	Intermediate Similarity	NPC111275
0.7193	Intermediate Similarity	NPC72905
0.7192	Intermediate Similarity	NPC47190
0.719	Intermediate Similarity	NPC315638
0.719	Intermediate Similarity	NPC313796
0.719	Intermediate Similarity	NPC314855
0.719	Intermediate Similarity	NPC313345
0.7186	Intermediate Similarity	NPC472119
0.7184	Intermediate Similarity	NPC477041
0.7184	Intermediate Similarity	NPC477044
0.7179	Intermediate Similarity	NPC110500
0.7179	Intermediate Similarity	NPC149155
0.7179	Intermediate Similarity	NPC203468
0.7178	Intermediate Similarity	NPC472112
0.7175	Intermediate Similarity	NPC475969
0.7175	Intermediate Similarity	NPC475859
0.7171	Intermediate Similarity	NPC245916
0.7171	Intermediate Similarity	NPC11445
0.7169	Intermediate Similarity	NPC210434
0.7168	Intermediate Similarity	NPC472061
0.7163	Intermediate Similarity	NPC146976
0.7162	Intermediate Similarity	NPC142385
0.7157	Intermediate Similarity	NPC283219
0.7157	Intermediate Similarity	NPC81802
0.7157	Intermediate Similarity	NPC269886
0.7157	Intermediate Similarity	NPC67659
0.7157	Intermediate Similarity	NPC472295
0.7157	Intermediate Similarity	NPC55772
0.7157	Intermediate Similarity	NPC247735
0.7157	Intermediate Similarity	NPC329541
0.7157	Intermediate Similarity	NPC472210
0.7156	Intermediate Similarity	NPC327769
0.7156	Intermediate Similarity	NPC183777
0.715	Intermediate Similarity	NPC295158
0.7143	Intermediate Similarity	NPC329708
0.7143	Intermediate Similarity	NPC289086
0.7143	Intermediate Similarity	NPC118832
0.7143	Intermediate Similarity	NPC88115
0.7143	Intermediate Similarity	NPC129721
0.7143	Intermediate Similarity	NPC165349
0.7143	Intermediate Similarity	NPC264166
0.7143	Intermediate Similarity	NPC274291

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 NPC328318 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	561
0.2-0.3	694
0.3-0.4	1541
0.4-0.5	2711
0.5-0.6	2111
0.6-0.7	1144
0.7-0.8	201
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
0.7882	Intermediate Similarity	NPD7666	Phase 3
0.7882	Intermediate Similarity	NPD7665	Phase 2
0.7871	Intermediate Similarity	NPD7001	Phase 3
0.7839	Intermediate Similarity	NPD6999	Discontinued
0.7839	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7783	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD8289	Discontinued
0.7692	Intermediate Similarity	NPD3794	Approved
0.7692	Intermediate Similarity	NPD3795	Approved
0.7647	Intermediate Similarity	NPD5901	Discontinued
0.7619	Intermediate Similarity	NPD3393	Approved
0.7619	Intermediate Similarity	NPD3394	Approved
0.7619	Intermediate Similarity	NPD3389	Approved
0.7576	Intermediate Similarity	NPD2336	Approved
0.7561	Intermediate Similarity	NPD8114	Approved
0.7561	Intermediate Similarity	NPD6987	Phase 1
0.7561	Intermediate Similarity	NPD8115	Approved
0.755	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD7944	Discontinued
0.7549	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD5862	Discovery
0.7476	Intermediate Similarity	NPD4852	Phase 2
0.7476	Intermediate Similarity	NPD6323	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD6204	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD8063	Discontinued
0.7433	Intermediate Similarity	NPD2511	Approved
0.7426	Intermediate Similarity	NPD2307	Discontinued
0.7426	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD5555	Phase 1
0.7411	Intermediate Similarity	NPD3082	Discontinued
0.7409	Intermediate Similarity	NPD5100	Phase 3
0.7404	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD5255	Approved
0.7374	Intermediate Similarity	NPD3315	Phase 3
0.7363	Intermediate Similarity	NPD5505	Discontinued
0.736	Intermediate Similarity	NPD7564	Discontinued
0.7358	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD6164	Phase 2
0.7352	Intermediate Similarity	NPD6165	Phase 2
0.7343	Intermediate Similarity	NPD4886	Phase 2
0.7337	Intermediate Similarity	NPD4948	Discontinued
0.732	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6137	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3280	Approved
0.7308	Intermediate Similarity	NPD5426	Phase 3
0.7306	Intermediate Similarity	NPD750	Phase 2
0.7299	Intermediate Similarity	NPD4051	Discontinued
0.7286	Intermediate Similarity	NPD2509	Approved
0.7286	Intermediate Similarity	NPD2510	Approved
0.7277	Intermediate Similarity	NPD3404	Approved
0.7273	Intermediate Similarity	NPD7568	Phase 1
0.7273	Intermediate Similarity	NPD6178	Phase 3
0.7273	Intermediate Similarity	NPD7010	Phase 3
0.7269	Intermediate Similarity	NPD7404	Approved
0.7268	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7204	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5475	Discontinued
0.7264	Intermediate Similarity	NPD3321	Discontinued
0.7263	Intermediate Similarity	NPD5088	Discontinued
0.726	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7817	Phase 1
0.7246	Intermediate Similarity	NPD7727	Phase 2
0.7231	Intermediate Similarity	NPD2382	Approved
0.7231	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD2381	Approved
0.7231	Intermediate Similarity	NPD2380	Approved
0.7229	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD7426	Phase 1
0.7225	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD2720	Phase 1
0.7222	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD7234	Approved
0.7214	Intermediate Similarity	NPD7233	Approved
0.7204	Intermediate Similarity	NPD6158	Phase 2
0.7204	Intermediate Similarity	NPD5965	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD2882	Phase 1
0.72	Intermediate Similarity	NPD5891	Approved
0.719	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD2091	Phase 2
0.7186	Intermediate Similarity	NPD2096	Phase 2
0.7186	Intermediate Similarity	NPD1096	Discontinued
0.7179	Intermediate Similarity	NPD482	Approved
0.7179	Intermediate Similarity	NPD5065	Approved
0.7178	Intermediate Similarity	NPD6281	Approved
0.7172	Intermediate Similarity	NPD8408	Discontinued
0.7171	Intermediate Similarity	NPD7061	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6995	Phase 1
0.7164	Intermediate Similarity	NPD4988	Discontinued
0.7164	Intermediate Similarity	NPD8021	Approved
0.7164	Intermediate Similarity	NPD8020	Approved
0.7158	Intermediate Similarity	NPD3813	Approved
0.7158	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD4639	Approved
0.715	Intermediate Similarity	NPD3330	Phase 1
0.715	Intermediate Similarity	NPD4640	Approved
0.715	Intermediate Similarity	NPD4638	Approved
0.7143	Intermediate Similarity	NPD7878	Phase 2
0.7143	Intermediate Similarity	NPD4038	Approved
0.7143	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4035	Approved
0.7143	Intermediate Similarity	NPD32	Approved
0.7143	Intermediate Similarity	NPD4037	Approved
0.7143	Intermediate Similarity	NPD4039	Approved
0.7143	Intermediate Similarity	NPD3947	Discontinued
0.7143	Intermediate Similarity	NPD4033	Approved
0.7143	Intermediate Similarity	NPD31	Approved
0.7143	Intermediate Similarity	NPD4034	Approved
0.7143	Intermediate Similarity	NPD3960	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4036	Approved
0.7143	Intermediate Similarity	NPD4429	Discontinued
0.7143	Intermediate Similarity	NPD4122	Approved
0.7136	Intermediate Similarity	NPD2094	Phase 2
0.7136	Intermediate Similarity	NPD3222	Phase 2
0.7136	Intermediate Similarity	NPD2092	Phase 2
0.7136	Intermediate Similarity	NPD2095	Phase 2
0.713	Intermediate Similarity	NPD5022	Discontinued
0.7123	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD4602	Approved
0.7115	Intermediate Similarity	NPD4601	Approved
0.7115	Intermediate Similarity	NPD6479	Discontinued
0.7115	Intermediate Similarity	NPD4600	Approved
0.7107	Intermediate Similarity	NPD8123	Approved
0.7107	Intermediate Similarity	NPD8122	Approved
0.7105	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD53	Approved
0.7101	Intermediate Similarity	NPD7777	Approved
0.7101	Intermediate Similarity	NPD7778	Approved
0.7098	Intermediate Similarity	NPD6446	Discontinued
0.7097	Intermediate Similarity	NPD3805	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD3178	Discontinued
0.7081	Intermediate Similarity	NPD5017	Discontinued
0.7074	Intermediate Similarity	NPD6790	Phase 1
0.7073	Intermediate Similarity	NPD5428	Discontinued
0.7073	Intermediate Similarity	NPD4526	Approved
0.7073	Intermediate Similarity	NPD4528	Approved
0.7073	Intermediate Similarity	NPD4529	Approved
0.7065	Intermediate Similarity	NPD6227	Discontinued
0.7062	Intermediate Similarity	NPD1343	Approved
0.7053	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7187	Phase 2
0.7047	Intermediate Similarity	NPD926	Approved
0.7047	Intermediate Similarity	NPD925	Approved
0.7044	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD4702	Approved
0.7043	Intermediate Similarity	NPD4547	Phase 3
0.7043	Intermediate Similarity	NPD1270	Approved
0.7043	Intermediate Similarity	NPD4703	Approved
0.7039	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5888	Phase 2
0.7037	Intermediate Similarity	NPD2823	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6595	Phase 3
0.7033	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7203	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5809	Phase 3
0.7024	Intermediate Similarity	NPD6569	Phase 2
0.7024	Intermediate Similarity	NPD4376	Phase 3
0.7023	Intermediate Similarity	NPD7470	Discontinued
0.7018	Intermediate Similarity	NPD8325	Phase 3
0.7018	Intermediate Similarity	NPD8326	Phase 3
0.7018	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6481	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6026	Approved
0.7	Intermediate Similarity	NPD6242	Discontinued
0.6995	Remote Similarity	NPD1631	Approved
0.6991	Remote Similarity	NPD8093	Discontinued
0.6991	Remote Similarity	NPD7069	Discontinued
0.6991	Remote Similarity	NPD7195	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7469	Discontinued
0.6984	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD2896	Discontinued
0.6978	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8321	Discontinued
0.6967	Remote Similarity	NPD6132	Phase 1
0.6965	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD4845	Discontinued
0.6963	Remote Similarity	NPD2582	Approved
0.6963	Remote Similarity	NPD2581	Approved
0.6959	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3243	Approved
0.6955	Remote Similarity	NPD7168	Phase 3
0.6954	Remote Similarity	NPD43	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