NPASS Compound

Structure

NPC71124 OpenBabel07101719512D 23 26 0 0 0 0 0 0 0 0999 V2000 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 -1.7321 -1.0000 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 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 -0.0000 -0.0000 0.0000 N 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 -4.4152 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 0.3090 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 1 0 0 0 0 7 12 1 0 0 0 0 8 20 1 0 0 0 0 9 14 2 0 0 0 0 9 17 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 22 1 0 0 0 0 11 23 1 0 0 0 0 13 14 1 0 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 17 18 2 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 20 1 0 0 0 0 19 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	293.14
Volume:	313.076
LogP:	4.543
LogD:	3.611
LogS:	-5.493
# Rotatable Bonds:	1
TPSA:	49.66
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.849
Synthetic Accessibility Score:	3.294
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.868
MDCK Permeability:	1.8822374840965495e-05
Pgp-inhibitor:	0.98
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.134
20% Bioavailability (F20%):	0.28
30% Bioavailability (F30%):	0.301

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.588
Plasma Protein Binding (PPB):	99.10803985595703%
Volume Distribution (VD):	0.961
Pgp-substrate:	1.1806758642196655%

ADMET: Metabolism

CYP1A2-inhibitor:	0.947
CYP1A2-substrate:	0.949
CYP2C19-inhibitor:	0.569
CYP2C19-substrate:	0.715
CYP2C9-inhibitor:	0.782
CYP2C9-substrate:	0.651
CYP2D6-inhibitor:	0.589
CYP2D6-substrate:	0.129
CYP3A4-inhibitor:	0.242
CYP3A4-substrate:	0.776

ADMET: Excretion

Clearance (CL):	0.436
Half-life (T1/2):	0.057

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.152
Drug-inuced Liver Injury (DILI):	0.914
AMES Toxicity:	0.182
Rat Oral Acute Toxicity:	0.385
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.707
Carcinogencity:	0.381
Eye Corrosion:	0.003
Eye Irritation:	0.413
Respiratory Toxicity:	0.907

Download Data

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

Natural Product: NPC71124

Natural Product ID:	NPC71124
*Common Name:**	N-Isopentylcrinasiadine
IUPAC Name:	5-(3-methylbutyl)-[1,3]dioxolo[4,5-j]phenanthridin-6-one
Synonyms:	N-Isopentylcrinasiadine
Standard InCHIKey:	RICZHCMSXSXKCY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H19NO3/c1-12(2)7-8-20-16-6-4-3-5-13(16)14-9-17-18(23-11-22-17)10-15(14)19(20)21/h3-6,9-10,12H,7-8,11H2,1-2H3
SMILES:	CC(CCn1c(=O)c2cc3OCOc3cc2c2c1cccc2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2208200
PubChem CID:	71452577
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004129] Phenanthridine- and phenanthridone-type amaryllidaceae alkaloids

*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
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	whole plants	n.a.	n.a.	PMID[23190013]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[23190013]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2348199]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26913788]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10671	Zephyranthes candida	Species	Amaryllidaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[502194]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[502194]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[502194]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	10000.0	nM	PMID[502194]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[502194]

☑ 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 NPC71124 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	515
0.1-0.2	2652
0.2-0.3	11946
0.3-0.4	5154
0.4-0.5	12443
0.5-0.6	7434
0.6-0.7	2076
0.7-0.8	419
0.8-0.85	39
0.85-0.9	8
0.9-0.95	6
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9771	High Similarity	NPC254957
0.9719	High Similarity	NPC5374
0.9613	High Similarity	NPC207971
0.956	High Similarity	NPC268077
0.8912	High Similarity	NPC55470
0.8571	High Similarity	NPC24954
0.8549	High Similarity	NPC308943
0.8508	High Similarity	NPC5167
0.8508	High Similarity	NPC85613
0.8387	Intermediate Similarity	NPC477259
0.8387	Intermediate Similarity	NPC169387
0.8378	Intermediate Similarity	NPC116007
0.8325	Intermediate Similarity	NPC193906
0.8325	Intermediate Similarity	NPC23080
0.8316	Intermediate Similarity	NPC207873
0.8316	Intermediate Similarity	NPC100573
0.8216	Intermediate Similarity	NPC27887
0.819	Intermediate Similarity	NPC253675
0.8182	Intermediate Similarity	NPC83511
0.8173	Intermediate Similarity	NPC222561
0.8142	Intermediate Similarity	NPC67978
0.8142	Intermediate Similarity	NPC303581
0.8132	Intermediate Similarity	NPC86469
0.8125	Intermediate Similarity	NPC477258
0.8114	Intermediate Similarity	NPC119669
0.8108	Intermediate Similarity	NPC287588
0.8108	Intermediate Similarity	NPC283810
0.8083	Intermediate Similarity	NPC24228
0.8054	Intermediate Similarity	NPC308267
0.8032	Intermediate Similarity	NPC249405
0.8011	Intermediate Similarity	NPC222524
0.7979	Intermediate Similarity	NPC179704
0.795	Intermediate Similarity	NPC90185
0.7921	Intermediate Similarity	NPC470708
0.7892	Intermediate Similarity	NPC298449
0.7882	Intermediate Similarity	NPC10732
0.7876	Intermediate Similarity	NPC226708
0.7872	Intermediate Similarity	NPC121400
0.7865	Intermediate Similarity	NPC312531
0.7864	Intermediate Similarity	NPC195120
0.7864	Intermediate Similarity	NPC87560
0.7838	Intermediate Similarity	NPC241055
0.7833	Intermediate Similarity	NPC82541
0.7817	Intermediate Similarity	NPC207239
0.7802	Intermediate Similarity	NPC135006
0.7773	Intermediate Similarity	NPC476436
0.7772	Intermediate Similarity	NPC231198
0.7772	Intermediate Similarity	NPC474904
0.776	Intermediate Similarity	NPC153631
0.775	Intermediate Similarity	NPC41216
0.774	Intermediate Similarity	NPC475959
0.7714	Intermediate Similarity	NPC148124
0.7713	Intermediate Similarity	NPC285941
0.7704	Intermediate Similarity	NPC469815
0.7704	Intermediate Similarity	NPC469816
0.7703	Intermediate Similarity	NPC118154
0.7703	Intermediate Similarity	NPC157983
0.7697	Intermediate Similarity	NPC470088
0.768	Intermediate Similarity	NPC208890
0.7677	Intermediate Similarity	NPC124302
0.7677	Intermediate Similarity	NPC215098
0.7677	Intermediate Similarity	NPC17677
0.7677	Intermediate Similarity	NPC70290
0.7677	Intermediate Similarity	NPC73020
0.7677	Intermediate Similarity	NPC46744
0.7677	Intermediate Similarity	NPC14622
0.7667	Intermediate Similarity	NPC99724
0.7653	Intermediate Similarity	NPC302001
0.7644	Intermediate Similarity	NPC313327
0.7632	Intermediate Similarity	NPC35680
0.7621	Intermediate Similarity	NPC159815
0.7621	Intermediate Similarity	NPC470482
0.7621	Intermediate Similarity	NPC470481
0.7604	Intermediate Similarity	NPC160113
0.7604	Intermediate Similarity	NPC476220
0.76	Intermediate Similarity	NPC226652
0.76	Intermediate Similarity	NPC72788
0.76	Intermediate Similarity	NPC314100
0.76	Intermediate Similarity	NPC120671
0.7596	Intermediate Similarity	NPC93653
0.7594	Intermediate Similarity	NPC471604
0.7593	Intermediate Similarity	NPC476429
0.7588	Intermediate Similarity	NPC100863
0.7582	Intermediate Similarity	NPC93593
0.7581	Intermediate Similarity	NPC306669
0.7581	Intermediate Similarity	NPC168409
0.7577	Intermediate Similarity	NPC21425
0.7576	Intermediate Similarity	NPC125924
0.7576	Intermediate Similarity	NPC33256
0.7571	Intermediate Similarity	NPC469978
0.757	Intermediate Similarity	NPC248903
0.7569	Intermediate Similarity	NPC154922
0.7568	Intermediate Similarity	NPC299582
0.7565	Intermediate Similarity	NPC102760
0.7558	Intermediate Similarity	NPC22481
0.7556	Intermediate Similarity	NPC223125
0.7554	Intermediate Similarity	NPC106786
0.7548	Intermediate Similarity	NPC146976
0.7541	Intermediate Similarity	NPC146288
0.7537	Intermediate Similarity	NPC38961
0.7527	Intermediate Similarity	NPC476569
0.7527	Intermediate Similarity	NPC59567
0.7525	Intermediate Similarity	NPC202771
0.7525	Intermediate Similarity	NPC328700
0.7525	Intermediate Similarity	NPC119818
0.7525	Intermediate Similarity	NPC2173
0.7523	Intermediate Similarity	NPC26928
0.7514	Intermediate Similarity	NPC160298
0.7514	Intermediate Similarity	NPC266753
0.7514	Intermediate Similarity	NPC232924
0.7514	Intermediate Similarity	NPC477559
0.7514	Intermediate Similarity	NPC306902
0.75	Intermediate Similarity	NPC236668
0.75	Intermediate Similarity	NPC190461
0.75	Intermediate Similarity	NPC141440
0.75	Intermediate Similarity	NPC45389
0.75	Intermediate Similarity	NPC278525
0.7488	Intermediate Similarity	NPC220241
0.7488	Intermediate Similarity	NPC295479
0.7487	Intermediate Similarity	NPC162653
0.7486	Intermediate Similarity	NPC41178
0.7486	Intermediate Similarity	NPC138487
0.7486	Intermediate Similarity	NPC216459
0.7475	Intermediate Similarity	NPC471489
0.7473	Intermediate Similarity	NPC223124
0.7473	Intermediate Similarity	NPC233029
0.7473	Intermediate Similarity	NPC210148
0.7466	Intermediate Similarity	NPC476258
0.7466	Intermediate Similarity	NPC304837
0.7463	Intermediate Similarity	NPC267414
0.7455	Intermediate Similarity	NPC189903
0.7455	Intermediate Similarity	NPC182907
0.7451	Intermediate Similarity	NPC475147
0.7436	Intermediate Similarity	NPC276674
0.7436	Intermediate Similarity	NPC33902
0.7435	Intermediate Similarity	NPC4669
0.7426	Intermediate Similarity	NPC138830
0.7426	Intermediate Similarity	NPC127178
0.7424	Intermediate Similarity	NPC63152
0.7424	Intermediate Similarity	NPC473004
0.7416	Intermediate Similarity	NPC268223
0.7411	Intermediate Similarity	NPC166979
0.7409	Intermediate Similarity	NPC108342
0.7404	Intermediate Similarity	NPC186569
0.7404	Intermediate Similarity	NPC61731
0.7399	Intermediate Similarity	NPC113455
0.7396	Intermediate Similarity	NPC287152
0.7394	Intermediate Similarity	NPC225774
0.7393	Intermediate Similarity	NPC126556
0.7391	Intermediate Similarity	NPC85661
0.7386	Intermediate Similarity	NPC314682
0.7377	Intermediate Similarity	NPC148898
0.7376	Intermediate Similarity	NPC212163
0.7371	Intermediate Similarity	NPC225745
0.7371	Intermediate Similarity	NPC470707
0.7371	Intermediate Similarity	NPC252107
0.7371	Intermediate Similarity	NPC318525
0.7371	Intermediate Similarity	NPC10653
0.736	Intermediate Similarity	NPC477186
0.736	Intermediate Similarity	NPC162694
0.7354	Intermediate Similarity	NPC476432
0.7354	Intermediate Similarity	NPC219341
0.7354	Intermediate Similarity	NPC24264
0.7351	Intermediate Similarity	NPC31311
0.7351	Intermediate Similarity	NPC234392
0.7345	Intermediate Similarity	NPC188163
0.7345	Intermediate Similarity	NPC474915
0.7345	Intermediate Similarity	NPC213206
0.7345	Intermediate Similarity	NPC328750
0.7343	Intermediate Similarity	NPC46679
0.734	Intermediate Similarity	NPC67904
0.7336	Intermediate Similarity	NPC46259
0.7333	Intermediate Similarity	NPC227361
0.7333	Intermediate Similarity	NPC124658
0.733	Intermediate Similarity	NPC474708
0.7327	Intermediate Similarity	NPC112937
0.7323	Intermediate Similarity	NPC237579
0.7316	Intermediate Similarity	NPC298979
0.7316	Intermediate Similarity	NPC247389
0.7314	Intermediate Similarity	NPC99078
0.7314	Intermediate Similarity	NPC7018
0.7313	Intermediate Similarity	NPC470646
0.7308	Intermediate Similarity	NPC475133
0.7308	Intermediate Similarity	NPC121510
0.7308	Intermediate Similarity	NPC171882
0.7308	Intermediate Similarity	NPC46990
0.7306	Intermediate Similarity	NPC207721
0.7304	Intermediate Similarity	NPC295676
0.7304	Intermediate Similarity	NPC303374
0.7302	Intermediate Similarity	NPC167546
0.7302	Intermediate Similarity	NPC16805
0.7302	Intermediate Similarity	NPC302527
0.7301	Intermediate Similarity	NPC120239
0.7297	Intermediate Similarity	NPC78733
0.7296	Intermediate Similarity	NPC473007
0.7292	Intermediate Similarity	NPC227683
0.7286	Intermediate Similarity	NPC1820
0.7277	Intermediate Similarity	NPC182853
0.7277	Intermediate Similarity	NPC475845
0.7273	Intermediate Similarity	NPC269449

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 NPC71124 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	649
0.2-0.3	960
0.3-0.4	1297
0.4-0.5	2677
0.5-0.6	2280
0.6-0.7	822
0.7-0.8	134
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8421	Intermediate Similarity	NPD5071	Phase 2
0.8122	Intermediate Similarity	NPD5186	Approved
0.8122	Intermediate Similarity	NPD5183	Approved
0.804	Intermediate Similarity	NPD4859	Phase 1
0.7989	Intermediate Similarity	NPD5977	Approved
0.7989	Intermediate Similarity	NPD5978	Approved
0.7958	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD7225	Discontinued
0.772	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD5950	Discontinued
0.7677	Intermediate Similarity	NPD4420	Approved
0.7668	Intermediate Similarity	NPD4084	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD8149	Discontinued
0.7565	Intermediate Similarity	NPD6618	Phase 2
0.7538	Intermediate Similarity	NPD7291	Discontinued
0.7534	Intermediate Similarity	NPD4846	Phase 2
0.7527	Intermediate Similarity	NPD7110	Phase 1
0.7527	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD5006	Approved
0.7525	Intermediate Similarity	NPD5005	Approved
0.7512	Intermediate Similarity	NPD4885	Approved
0.75	Intermediate Similarity	NPD3641	Approved
0.75	Intermediate Similarity	NPD3639	Approved
0.75	Intermediate Similarity	NPD3640	Phase 3
0.7488	Intermediate Similarity	NPD683	Approved
0.7475	Intermediate Similarity	NPD6321	Discontinued
0.7474	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD3349	Phase 2
0.7435	Intermediate Similarity	NPD5312	Approved
0.7435	Intermediate Similarity	NPD5313	Approved
0.7429	Intermediate Similarity	NPD5025	Approved
0.7423	Intermediate Similarity	NPD7280	Phase 3
0.7423	Intermediate Similarity	NPD7281	Phase 3
0.7418	Intermediate Similarity	NPD824	Approved
0.7415	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5582	Discontinued
0.7397	Intermediate Similarity	NPD6625	Approved
0.7345	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD5600	Discontinued
0.7333	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD5900	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD6457	Approved
0.7286	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6876	Approved
0.7283	Intermediate Similarity	NPD6875	Approved
0.7277	Intermediate Similarity	NPD5564	Approved
0.7277	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD7279	Phase 2
0.7269	Intermediate Similarity	NPD7278	Phase 2
0.7268	Intermediate Similarity	NPD6297	Approved
0.7264	Intermediate Similarity	NPD6493	Phase 3
0.7263	Intermediate Similarity	NPD4166	Phase 2
0.7257	Intermediate Similarity	NPD2492	Phase 1
0.7255	Intermediate Similarity	NPD5457	Discontinued
0.7254	Intermediate Similarity	NPD5521	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7597	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD7559	Phase 2
0.7202	Intermediate Similarity	NPD7223	Discontinued
0.7202	Intermediate Similarity	NPD7224	Discontinued
0.7186	Intermediate Similarity	NPD5620	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6293	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6654	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6386	Approved
0.7151	Intermediate Similarity	NPD6385	Approved
0.715	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7449	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6238	Discontinued
0.7122	Intermediate Similarity	NPD1880	Phase 3
0.7121	Intermediate Similarity	NPD6853	Approved
0.7121	Intermediate Similarity	NPD6851	Approved
0.712	Intermediate Similarity	NPD2821	Approved
0.7104	Intermediate Similarity	NPD4584	Approved
0.7087	Intermediate Similarity	NPD4107	Approved
0.7083	Intermediate Similarity	NPD2899	Discontinued
0.7081	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD2968	Approved
0.7071	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD2971	Approved
0.7053	Intermediate Similarity	NPD1307	Phase 2
0.7053	Intermediate Similarity	NPD1309	Phase 2
0.7051	Intermediate Similarity	NPD3437	Discontinued
0.7047	Intermediate Similarity	NPD5242	Approved
0.7042	Intermediate Similarity	NPD3816	Phase 1
0.7042	Intermediate Similarity	NPD3815	Phase 1
0.7041	Intermediate Similarity	NPD3920	Phase 2
0.7034	Intermediate Similarity	NPD7708	Approved
0.7033	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1670	Discontinued
0.7027	Intermediate Similarity	NPD6031	Approved
0.7027	Intermediate Similarity	NPD6030	Approved
0.7022	Intermediate Similarity	NPD743	Approved
0.7018	Intermediate Similarity	NPD6716	Phase 1
0.698	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD4482	Phase 3
0.6968	Remote Similarity	NPD6873	Phase 2
0.6965	Remote Similarity	NPD4515	Suspended
0.6957	Remote Similarity	NPD6874	Approved
0.6955	Remote Similarity	NPD3912	Discontinued
0.6952	Remote Similarity	NPD4017	Approved
0.6952	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD8091	Phase 3
0.6948	Remote Similarity	NPD5860	Discontinued
0.6948	Remote Similarity	NPD5914	Approved
0.6943	Remote Similarity	NPD3983	Phase 3
0.6943	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5515	Phase 2
0.6938	Remote Similarity	NPD3057	Approved
0.6938	Remote Similarity	NPD7627	Approved
0.6938	Remote Similarity	NPD7626	Approved
0.6933	Remote Similarity	NPD6723	Discontinued
0.6931	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5997	Discontinued
0.6917	Remote Similarity	NPD7803	Approved
0.6916	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD3924	Approved
0.6912	Remote Similarity	NPD3921	Approved
0.6912	Remote Similarity	NPD3923	Approved
0.6912	Remote Similarity	NPD3922	Approved
0.6904	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6146	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD3257	Approved
0.6897	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD3964	Approved
0.6878	Remote Similarity	NPD6181	Discontinued
0.6869	Remote Similarity	NPD7479	Phase 2
0.6863	Remote Similarity	NPD2488	Approved
0.6863	Remote Similarity	NPD2490	Approved
0.6862	Remote Similarity	NPD6357	Discontinued
0.6859	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3533	Approved
0.6857	Remote Similarity	NPD3448	Approved
0.6857	Remote Similarity	NPD2972	Approved
0.6857	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2491	Approved
0.6856	Remote Similarity	NPD6107	Approved
0.6856	Remote Similarity	NPD2680	Approved
0.6856	Remote Similarity	NPD2681	Approved
0.6849	Remote Similarity	NPD3258	Approved
0.6849	Remote Similarity	NPD5519	Discontinued
0.6848	Remote Similarity	NPD3301	Approved
0.6845	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5805	Approved
0.6842	Remote Similarity	NPD7298	Approved
0.6842	Remote Similarity	NPD3290	Approved
0.6842	Remote Similarity	NPD3289	Phase 3
0.6837	Remote Similarity	NPD2898	Approved
0.6818	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5928	Phase 1
0.6806	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5823	Approved
0.6802	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4952	Phase 3
0.68	Remote Similarity	NPD4981	Phase 2
0.6797	Remote Similarity	NPD6517	Phase 3
0.6787	Remote Similarity	NPD7805	Phase 3
0.6786	Remote Similarity	NPD4328	Approved
0.6784	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD5658	Approved
0.6776	Remote Similarity	NPD8027	Approved
0.6776	Remote Similarity	NPD4082	Approved
0.6774	Remote Similarity	NPD4356	Discontinued
0.6773	Remote Similarity	NPD3763	Approved
0.6772	Remote Similarity	NPD3229	Phase 2
0.6771	Remote Similarity	NPD5967	Approved
0.6771	Remote Similarity	NPD2358	Clinical (unspecified phase)
0.677	Remote Similarity	NPD3442	Approved
0.677	Remote Similarity	NPD3441	Approved
0.6768	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD6612	Phase 2
0.6757	Remote Similarity	NPD8311	Discontinued
0.6757	Remote Similarity	NPD6997	Phase 2
0.6753	Remote Similarity	NPD4796	Discontinued
0.6753	Remote Similarity	NPD6790	Phase 1
0.675	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD7186	Phase 3
0.674	Remote Similarity	NPD2670	Approved
0.6739	Remote Similarity	NPD2820	Phase 3
0.6736	Remote Similarity	NPD1742	Approved
0.6736	Remote Similarity	NPD19	Approved
0.6736	Remote Similarity	NPD1743	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