NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	241.07
Volume:	243.943
LogP:	3.488
LogD:	2.807
LogS:	-3.634
# Rotatable Bonds:	2
TPSA:	62.32
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.724
Synthetic Accessibility Score:	1.851
Fsp3:	0.071
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.901
MDCK Permeability:	6.45508816887741e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.726

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.325
Plasma Protein Binding (PPB):	88.93181610107422%
Volume Distribution (VD):	0.616
Pgp-substrate:	8.39086627960205%

ADMET: Metabolism

CYP1A2-inhibitor:	0.667
CYP1A2-substrate:	0.835
CYP2C19-inhibitor:	0.097
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.07
CYP2C9-substrate:	0.295
CYP2D6-inhibitor:	0.394
CYP2D6-substrate:	0.143
CYP3A4-inhibitor:	0.057
CYP3A4-substrate:	0.073

ADMET: Excretion

Clearance (CL):	2.201
Half-life (T1/2):	0.81

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.734
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.094
Rat Oral Acute Toxicity:	0.401
Maximum Recommended Daily Dose:	0.829
Skin Sensitization:	0.481
Carcinogencity:	0.75
Eye Corrosion:	0.006
Eye Irritation:	0.972
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC87413

Natural Product ID:	NPC87413
*Common Name:**	Clausine N
IUPAC Name:	7-methoxy-9H-carbazole-3-carboxylic acid
Synonyms:
Standard InCHIKey:	USLLRQCTAZQWLY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H11NO3/c1-18-9-3-4-10-11-6-8(14(16)17)2-5-12(11)15-13(10)7-9/h2-7,15H,1H3,(H,16,17)
SMILES:	COc1ccc2c(c1)[nH]c1c2cc(cc1)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2260662
PubChem CID:	11954806
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

*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
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000023]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19266	Clausena excavata	Species	Rutaceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC90	>	128000.0	nM	PMID[469906]

☑ 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 NPC87413 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	412
0.1-0.2	2781
0.2-0.3	11655
0.3-0.4	4957
0.4-0.5	14956
0.5-0.6	5321
0.6-0.7	1886
0.7-0.8	623
0.8-0.85	67
0.85-0.9	24
0.9-0.95	11
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9786	High Similarity	NPC4687
0.9734	High Similarity	NPC39679
0.959	High Similarity	NPC174760
0.9474	High Similarity	NPC249583
0.9433	High Similarity	NPC116238
0.9388	High Similarity	NPC247803
0.9385	High Similarity	NPC3207
0.9337	High Similarity	NPC169402
0.9293	High Similarity	NPC150239
0.9231	High Similarity	NPC308137
0.9231	High Similarity	NPC310211
0.9219	High Similarity	NPC300156
0.9109	High Similarity	NPC179287
0.9095	High Similarity	NPC184408
0.9	High Similarity	NPC46561
0.8955	High Similarity	NPC208084
0.8929	High Similarity	NPC210828
0.8929	High Similarity	NPC86834
0.8923	High Similarity	NPC45190
0.8894	High Similarity	NPC39500
0.8889	High Similarity	NPC23294
0.8867	High Similarity	NPC198503
0.885	High Similarity	NPC118228
0.8838	High Similarity	NPC303951
0.8824	High Similarity	NPC160381
0.8802	High Similarity	NPC243834
0.8802	High Similarity	NPC70956
0.8792	High Similarity	NPC274640
0.8732	High Similarity	NPC144452
0.8689	High Similarity	NPC51388
0.8687	High Similarity	NPC321428
0.8679	High Similarity	NPC6786
0.8607	High Similarity	NPC187501
0.8592	High Similarity	NPC280799
0.8505	High Similarity	NPC131017
0.8485	Intermediate Similarity	NPC475085
0.8485	Intermediate Similarity	NPC475112
0.8485	Intermediate Similarity	NPC291535
0.8469	Intermediate Similarity	NPC306376
0.8458	Intermediate Similarity	NPC473187
0.8454	Intermediate Similarity	NPC225279
0.8447	Intermediate Similarity	NPC473041
0.8443	Intermediate Similarity	NPC474701
0.8443	Intermediate Similarity	NPC474688
0.8413	Intermediate Similarity	NPC60621
0.8408	Intermediate Similarity	NPC193777
0.8387	Intermediate Similarity	NPC475844
0.8376	Intermediate Similarity	NPC72211
0.8368	Intermediate Similarity	NPC212535
0.8358	Intermediate Similarity	NPC476106
0.835	Intermediate Similarity	NPC134848
0.8333	Intermediate Similarity	NPC9894
0.8317	Intermediate Similarity	NPC283117
0.8281	Intermediate Similarity	NPC94943
0.8274	Intermediate Similarity	NPC70259
0.8263	Intermediate Similarity	NPC194740
0.8261	Intermediate Similarity	NPC330009
0.8244	Intermediate Similarity	NPC294375
0.8229	Intermediate Similarity	NPC190007
0.8229	Intermediate Similarity	NPC84478
0.8223	Intermediate Similarity	NPC205934
0.8223	Intermediate Similarity	NPC43787
0.8221	Intermediate Similarity	NPC293151
0.8209	Intermediate Similarity	NPC135887
0.8209	Intermediate Similarity	NPC199277
0.8182	Intermediate Similarity	NPC303658
0.8173	Intermediate Similarity	NPC152768
0.8173	Intermediate Similarity	NPC148183
0.8168	Intermediate Similarity	NPC162484
0.815	Intermediate Similarity	NPC128823
0.8122	Intermediate Similarity	NPC21638
0.8116	Intermediate Similarity	NPC48353
0.8111	Intermediate Similarity	NPC473105
0.8102	Intermediate Similarity	NPC260434
0.8093	Intermediate Similarity	NPC471762
0.8075	Intermediate Similarity	NPC122436
0.8058	Intermediate Similarity	NPC325297
0.8009	Intermediate Similarity	NPC96321
0.8	Intermediate Similarity	NPC89549
0.798	Intermediate Similarity	NPC476044
0.798	Intermediate Similarity	NPC267423
0.7972	Intermediate Similarity	NPC473179
0.797	Intermediate Similarity	NPC242928
0.7962	Intermediate Similarity	NPC305984
0.7961	Intermediate Similarity	NPC183777
0.796	Intermediate Similarity	NPC153042
0.795	Intermediate Similarity	NPC276517
0.7943	Intermediate Similarity	NPC12344
0.7931	Intermediate Similarity	NPC329747
0.7929	Intermediate Similarity	NPC83111
0.7927	Intermediate Similarity	NPC72980
0.7927	Intermediate Similarity	NPC88363
0.7926	Intermediate Similarity	NPC66777
0.7923	Intermediate Similarity	NPC475910
0.7909	Intermediate Similarity	NPC39370
0.7906	Intermediate Similarity	NPC474409
0.7905	Intermediate Similarity	NPC89508
0.7902	Intermediate Similarity	NPC165599
0.79	Intermediate Similarity	NPC473186
0.79	Intermediate Similarity	NPC132329
0.7897	Intermediate Similarity	NPC477532
0.7887	Intermediate Similarity	NPC74360
0.7885	Intermediate Similarity	NPC209769
0.7885	Intermediate Similarity	NPC201697
0.7871	Intermediate Similarity	NPC141454
0.787	Intermediate Similarity	NPC97746
0.7868	Intermediate Similarity	NPC194040
0.784	Intermediate Similarity	NPC264285
0.7838	Intermediate Similarity	NPC235685
0.7832	Intermediate Similarity	NPC475666
0.783	Intermediate Similarity	NPC469928
0.7818	Intermediate Similarity	NPC475720
0.7818	Intermediate Similarity	NPC474192
0.7816	Intermediate Similarity	NPC223427
0.781	Intermediate Similarity	NPC146418
0.7803	Intermediate Similarity	NPC101350
0.7793	Intermediate Similarity	NPC312645
0.7788	Intermediate Similarity	NPC81939
0.7778	Intermediate Similarity	NPC470930
0.7778	Intermediate Similarity	NPC132539
0.7767	Intermediate Similarity	NPC323969
0.7763	Intermediate Similarity	NPC91868
0.7763	Intermediate Similarity	NPC63971
0.7762	Intermediate Similarity	NPC471304
0.7762	Intermediate Similarity	NPC11464
0.7756	Intermediate Similarity	NPC213308
0.7746	Intermediate Similarity	NPC74969
0.7732	Intermediate Similarity	NPC84347
0.7729	Intermediate Similarity	NPC165964
0.7729	Intermediate Similarity	NPC476098
0.7723	Intermediate Similarity	NPC475190
0.7721	Intermediate Similarity	NPC298436
0.7718	Intermediate Similarity	NPC232727
0.7717	Intermediate Similarity	NPC473185
0.7717	Intermediate Similarity	NPC478078
0.7716	Intermediate Similarity	NPC176127
0.7709	Intermediate Similarity	NPC78609
0.7707	Intermediate Similarity	NPC280714
0.7703	Intermediate Similarity	NPC244741
0.7703	Intermediate Similarity	NPC270918
0.7696	Intermediate Similarity	NPC473188
0.7696	Intermediate Similarity	NPC16352
0.7692	Intermediate Similarity	NPC285558
0.7689	Intermediate Similarity	NPC264176
0.7689	Intermediate Similarity	NPC475816
0.7685	Intermediate Similarity	NPC472099
0.7682	Intermediate Similarity	NPC252251
0.7682	Intermediate Similarity	NPC311906
0.7679	Intermediate Similarity	NPC15801
0.7675	Intermediate Similarity	NPC469734
0.7671	Intermediate Similarity	NPC470018
0.7667	Intermediate Similarity	NPC470931
0.7665	Intermediate Similarity	NPC474798
0.7653	Intermediate Similarity	NPC469592
0.7653	Intermediate Similarity	NPC471080
0.7644	Intermediate Similarity	NPC470784
0.7639	Intermediate Similarity	NPC213530
0.7639	Intermediate Similarity	NPC193267
0.7636	Intermediate Similarity	NPC157931
0.7619	Intermediate Similarity	NPC193238
0.7615	Intermediate Similarity	NPC220851
0.7613	Intermediate Similarity	NPC477531
0.7612	Intermediate Similarity	NPC246700
0.76	Intermediate Similarity	NPC184680
0.7594	Intermediate Similarity	NPC470020
0.7594	Intermediate Similarity	NPC269367
0.759	Intermediate Similarity	NPC303225
0.7588	Intermediate Similarity	NPC62069
0.7581	Intermediate Similarity	NPC170114
0.7568	Intermediate Similarity	NPC209174
0.7566	Intermediate Similarity	NPC470785
0.7563	Intermediate Similarity	NPC100734
0.7563	Intermediate Similarity	NPC88923
0.7563	Intermediate Similarity	NPC315634
0.7562	Intermediate Similarity	NPC46580
0.7561	Intermediate Similarity	NPC251090
0.7555	Intermediate Similarity	NPC160898
0.7549	Intermediate Similarity	NPC230403
0.7545	Intermediate Similarity	NPC473182
0.7537	Intermediate Similarity	NPC138370
0.7535	Intermediate Similarity	NPC470549
0.7523	Intermediate Similarity	NPC477533
0.7523	Intermediate Similarity	NPC316981
0.7512	Intermediate Similarity	NPC123976
0.7512	Intermediate Similarity	NPC469594
0.7512	Intermediate Similarity	NPC167860
0.7512	Intermediate Similarity	NPC199667
0.7512	Intermediate Similarity	NPC295898
0.75	Intermediate Similarity	NPC322064
0.75	Intermediate Similarity	NPC315491
0.75	Intermediate Similarity	NPC45459
0.75	Intermediate Similarity	NPC284685
0.7478	Intermediate Similarity	NPC208522
0.7477	Intermediate Similarity	NPC220337
0.7477	Intermediate Similarity	NPC74575
0.7476	Intermediate Similarity	NPC13880
0.7474	Intermediate Similarity	NPC76982
0.7465	Intermediate Similarity	NPC473181
0.7464	Intermediate Similarity	NPC471944
0.7463	Intermediate Similarity	NPC307963

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 NPC87413 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	668
0.2-0.3	910
0.3-0.4	1239
0.4-0.5	2761
0.5-0.6	2244
0.6-0.7	879
0.7-0.8	155
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD5632	Approved
0.8213	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD3258	Approved
0.7972	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD3259	Approved
0.7951	Intermediate Similarity	NPD5901	Discontinued
0.7936	Intermediate Similarity	NPD6962	Phase 2
0.7867	Intermediate Similarity	NPD3257	Approved
0.7848	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD5512	Phase 3
0.781	Intermediate Similarity	NPD5416	Discontinued
0.7783	Intermediate Similarity	NPD4373	Phase 2
0.7767	Intermediate Similarity	NPD6242	Discontinued
0.7727	Intermediate Similarity	NPD4952	Phase 3
0.7696	Intermediate Similarity	NPD5003	Discontinued
0.7675	Intermediate Similarity	NPD5488	Discontinued
0.7674	Intermediate Similarity	NPD7395	Discontinued
0.7667	Intermediate Similarity	NPD5658	Approved
0.7656	Intermediate Similarity	NPD3003	Approved
0.7655	Intermediate Similarity	NPD6790	Phase 1
0.7652	Intermediate Similarity	NPD5482	Discontinued
0.7636	Intermediate Similarity	NPD4328	Approved
0.7619	Intermediate Similarity	NPD5429	Discontinued
0.7574	Intermediate Similarity	NPD2564	Approved
0.7574	Intermediate Similarity	NPD2565	Phase 2
0.7563	Intermediate Similarity	NPD7803	Approved
0.7562	Intermediate Similarity	NPD4948	Discontinued
0.7557	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7555	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1867	Approved
0.7522	Intermediate Similarity	NPD5805	Approved
0.7512	Intermediate Similarity	NPD4418	Discontinued
0.75	Intermediate Similarity	NPD484	Approved
0.75	Intermediate Similarity	NPD7956	Approved
0.75	Intermediate Similarity	NPD7955	Approved
0.75	Intermediate Similarity	NPD7417	Discontinued
0.7474	Intermediate Similarity	NPD2844	Phase 3
0.7469	Intermediate Similarity	NPD8363	Approved
0.7469	Intermediate Similarity	NPD8364	Approved
0.7467	Intermediate Similarity	NPD6716	Phase 1
0.7463	Intermediate Similarity	NPD1038	Approved
0.7452	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD1768	Approved
0.7442	Intermediate Similarity	NPD5866	Approved
0.743	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD4885	Approved
0.7418	Intermediate Similarity	NPD2916	Discontinued
0.7407	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7406	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7853	Phase 2
0.7399	Intermediate Similarity	NPD7994	Phase 2
0.7395	Intermediate Similarity	NPD7708	Approved
0.7395	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD3925	Approved
0.7383	Intermediate Similarity	NPD4506	Discontinued
0.7376	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD5903	Approved
0.7373	Intermediate Similarity	NPD5902	Approved
0.7361	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD7069	Discontinued
0.7358	Intermediate Similarity	NPD8465	Approved
0.7358	Intermediate Similarity	NPD8428	Approved
0.7358	Intermediate Similarity	NPD8429	Approved
0.7358	Intermediate Similarity	NPD8427	Approved
0.7358	Intermediate Similarity	NPD8467	Approved
0.7358	Intermediate Similarity	NPD8466	Approved
0.7352	Intermediate Similarity	NPD3354	Phase 2
0.7347	Intermediate Similarity	NPD1326	Approved
0.7347	Intermediate Similarity	NPD1325	Approved
0.7342	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD6530	Approved
0.7322	Intermediate Similarity	NPD6531	Approved
0.7315	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD8091	Phase 3
0.7297	Intermediate Similarity	NPD6995	Phase 1
0.7295	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5450	Discontinued
0.7268	Intermediate Similarity	NPD1534	Approved
0.7265	Intermediate Similarity	NPD8358	Approved
0.7264	Intermediate Similarity	NPD2779	Approved
0.726	Intermediate Similarity	NPD5612	Discontinued
0.726	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5479	Discontinued
0.724	Intermediate Similarity	NPD8425	Approved
0.724	Intermediate Similarity	NPD8459	Approved
0.724	Intermediate Similarity	NPD8460	Approved
0.724	Intermediate Similarity	NPD8426	Approved
0.723	Intermediate Similarity	NPD6176	Phase 1
0.7225	Intermediate Similarity	NPD1466	Phase 3
0.7225	Intermediate Similarity	NPD1505	Phase 2
0.7225	Intermediate Similarity	NPD1467	Approved
0.7209	Intermediate Similarity	NPD1392	Approved
0.7203	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD3947	Discontinued
0.7195	Intermediate Similarity	NPD4429	Discontinued
0.7189	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD8463	Approved
0.7176	Intermediate Similarity	NPD6376	Discontinued
0.7176	Intermediate Similarity	NPD2509	Approved
0.7176	Intermediate Similarity	NPD2510	Approved
0.717	Intermediate Similarity	NPD3289	Phase 3
0.717	Intermediate Similarity	NPD4500	Approved
0.717	Intermediate Similarity	NPD4501	Approved
0.717	Intermediate Similarity	NPD3290	Approved
0.7169	Intermediate Similarity	NPD3243	Approved
0.7163	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6770	Approved
0.7162	Intermediate Similarity	NPD7558	Phase 2
0.7161	Intermediate Similarity	NPD8102	Discontinued
0.7156	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7470	Discontinued
0.7156	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD2920	Discontinued
0.7143	Intermediate Similarity	NPD4368	Phase 2
0.7136	Intermediate Similarity	NPD4511	Phase 1
0.713	Intermediate Similarity	NPD7453	Approved
0.713	Intermediate Similarity	NPD7222	Phase 2
0.713	Intermediate Similarity	NPD7452	Approved
0.7129	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD4539	Phase 1
0.7123	Intermediate Similarity	NPD2778	Approved
0.7119	Intermediate Similarity	NPD5399	Discovery
0.7118	Intermediate Similarity	NPD3746	Discontinued
0.7117	Intermediate Similarity	NPD6985	Discontinued
0.7117	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7116	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD7948	Phase 1
0.7109	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD3006	Discontinued
0.7095	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6517	Phase 3
0.7094	Intermediate Similarity	NPD5445	Approved
0.7089	Intermediate Similarity	NPD4601	Approved
0.7089	Intermediate Similarity	NPD4600	Approved
0.7087	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD4312	Approved
0.7085	Intermediate Similarity	NPD6974	Phase 3
0.7085	Intermediate Similarity	NPD7194	Discontinued
0.7083	Intermediate Similarity	NPD8403	Phase 1
0.7081	Intermediate Similarity	NPD5937	Approved
0.7075	Intermediate Similarity	NPD7946	Pre-registration
0.7074	Intermediate Similarity	NPD7688	Phase 1
0.7073	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4499	Approved
0.7062	Intermediate Similarity	NPD6550	Discontinued
0.7059	Intermediate Similarity	NPD5293	Phase 2
0.7056	Intermediate Similarity	NPD7689	Approved
0.7054	Intermediate Similarity	NPD7180	Phase 3
0.7044	Intermediate Similarity	NPD3920	Phase 2
0.704	Intermediate Similarity	NPD1926	Approved
0.7039	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6323	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6987	Phase 1
0.7037	Intermediate Similarity	NPD6228	Discontinued
0.7031	Intermediate Similarity	NPD5022	Discontinued
0.703	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD6988	Phase 1
0.7027	Intermediate Similarity	NPD8160	Phase 2
0.7019	Intermediate Similarity	NPD2792	Approved
0.7017	Intermediate Similarity	NPD4558	Phase 2
0.7014	Intermediate Similarity	NPD3945	Discontinued
0.7014	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5067	Phase 2
0.7	Intermediate Similarity	NPD5066	Phase 2
0.6996	Remote Similarity	NPD5164	Discontinued
0.6996	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD3986	Discontinued
0.6987	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.698	Remote Similarity	NPD482	Approved
0.6976	Remote Similarity	NPD4204	Approved
0.6976	Remote Similarity	NPD4203	Approved
0.6974	Remote Similarity	NPD3263	Phase 3
0.6967	Remote Similarity	NPD802	Phase 2
0.6967	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7878	Phase 2
0.6963	Remote Similarity	NPD3825	Phase 3
0.6955	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3393	Approved
0.6951	Remote Similarity	NPD3389	Approved
0.6951	Remote Similarity	NPD3394	Approved
0.6946	Remote Similarity	NPD7658	Phase 2
0.6943	Remote Similarity	NPD4845	Discontinued
0.6939	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3794	Approved
0.6937	Remote Similarity	NPD3795	Approved
0.6937	Remote Similarity	NPD4356	Discontinued
0.6936	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD8489	Phase 1
0.6934	Remote Similarity	NPD6590	Discontinued
0.6927	Remote Similarity	NPD5530	Phase 1

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