NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	227.06
Volume:	226.647
LogP:	2.844
LogD:	2.634
LogS:	-4.273
# Rotatable Bonds:	1
TPSA:	73.32
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.559
Synthetic Accessibility Score:	2.52
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.078
MDCK Permeability:	4.796409939444857e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.125
20% Bioavailability (F20%):	0.943
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.079
Plasma Protein Binding (PPB):	94.7927474975586%
Volume Distribution (VD):	0.688
Pgp-substrate:	3.6096200942993164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.989
CYP1A2-substrate:	0.15
CYP2C19-inhibitor:	0.132
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.112
CYP2C9-substrate:	0.904
CYP2D6-inhibitor:	0.584
CYP2D6-substrate:	0.798
CYP3A4-inhibitor:	0.528
CYP3A4-substrate:	0.106

ADMET: Excretion

Clearance (CL):	7.29
Half-life (T1/2):	0.739

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.105
Drug-inuced Liver Injury (DILI):	0.721
AMES Toxicity:	0.659
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.926
Carcinogencity:	0.329
Eye Corrosion:	0.2
Eye Irritation:	0.982
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC86834

Natural Product ID:	NPC86834
*Common Name:**	Clausine O
IUPAC Name:	2,7-dihydroxy-9H-carbazole-3-carbaldehyde
Synonyms:	Clausine O
Standard InCHIKey:	RTRVKTRUQDUIKV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H9NO3/c15-6-7-3-10-9-2-1-8(16)4-11(9)14-12(10)5-13(7)17/h1-6,14,16-17H
SMILES:	c1cc2c3cc(C=O)c(cc3[nH]c2cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689804
PubChem CID:	11241634
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]
NPO21978	Clausena harmandiana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO21978	Clausena harmandiana	Species	Rutaceae	Eukaryota	n.a.	root	n.a.	PMID[21302964]
NPO18135	Clausena vestita	Species	Rutaceae	Eukaryota	whole plants	Yunnan Province, China	2008-JAN	PMID[22093759]
NPO21978	Clausena harmandiana	Species	Rutaceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3236015]
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]
NPO18135	Clausena vestita	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21978	Clausena harmandiana	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
IC50	5
MIC	1
Others	2

Activity Type	# Activity
Cell Line	5
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	74730.0	nM	PMID[484950]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	59550.0	nM	PMID[484950]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	64610.0	nM	PMID[484950]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	32800.0	nM	PMID[484951]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	114000.0	nM	PMID[484953]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	25.0	ug.mL-1	PMID[484952]
NPT2	Others	Unspecified		Selectivity Index	=	1.3	n.a.	PMID[484953]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC90	=	89000.0	nM	PMID[484953]

☑ 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 NPC86834 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	529
0.1-0.2	3370
0.2-0.3	13335
0.3-0.4	4833
0.4-0.5	15012
0.5-0.6	3518
0.6-0.7	1692
0.7-0.8	356
0.8-0.85	23
0.85-0.9	18
0.9-0.95	6
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC210828
0.984	High Similarity	NPC23294
0.9786	High Similarity	NPC303951
0.9534	High Similarity	NPC247803
0.9436	High Similarity	NPC150239
0.933	High Similarity	NPC3207
0.9275	High Similarity	NPC308137
0.9275	High Similarity	NPC310211
0.9167	High Similarity	NPC39679
0.9045	High Similarity	NPC174760
0.904	High Similarity	NPC46561
0.9016	High Similarity	NPC249583
0.8929	High Similarity	NPC9894
0.8929	High Similarity	NPC87413
0.8905	High Similarity	NPC198503
0.8889	High Similarity	NPC116238
0.8821	High Similarity	NPC283117
0.8804	High Similarity	NPC6786
0.88	High Similarity	NPC169402
0.8775	High Similarity	NPC179287
0.8737	High Similarity	NPC294375
0.8724	High Similarity	NPC4687
0.8703	High Similarity	NPC212535
0.8614	High Similarity	NPC293151
0.861	High Similarity	NPC94943
0.8578	High Similarity	NPC473187
0.8556	High Similarity	NPC190007
0.8529	High Similarity	NPC208084
0.8485	Intermediate Similarity	NPC45190
0.8477	Intermediate Similarity	NPC134848
0.8442	Intermediate Similarity	NPC183777
0.8359	Intermediate Similarity	NPC243834
0.8359	Intermediate Similarity	NPC70956
0.8333	Intermediate Similarity	NPC118228
0.8324	Intermediate Similarity	NPC474409
0.8316	Intermediate Similarity	NPC306376
0.8265	Intermediate Similarity	NPC153042
0.8209	Intermediate Similarity	NPC300156
0.819	Intermediate Similarity	NPC51388
0.8186	Intermediate Similarity	NPC187501
0.8177	Intermediate Similarity	NPC160381
0.8146	Intermediate Similarity	NPC12344
0.8125	Intermediate Similarity	NPC184408
0.8106	Intermediate Similarity	NPC89549
0.8093	Intermediate Similarity	NPC132329
0.806	Intermediate Similarity	NPC475085
0.806	Intermediate Similarity	NPC475112
0.806	Intermediate Similarity	NPC291535
0.8053	Intermediate Similarity	NPC72980
0.8053	Intermediate Similarity	NPC88363
0.8048	Intermediate Similarity	NPC225279
0.8047	Intermediate Similarity	NPC474701
0.8038	Intermediate Similarity	NPC264285
0.8029	Intermediate Similarity	NPC330009
0.8	Intermediate Similarity	NPC325297
0.799	Intermediate Similarity	NPC193777
0.798	Intermediate Similarity	NPC131017
0.7941	Intermediate Similarity	NPC476106
0.7933	Intermediate Similarity	NPC39500
0.7908	Intermediate Similarity	NPC246700
0.7902	Intermediate Similarity	NPC270918
0.7889	Intermediate Similarity	NPC276517
0.788	Intermediate Similarity	NPC76982
0.787	Intermediate Similarity	NPC274640
0.7864	Intermediate Similarity	NPC171787
0.7861	Intermediate Similarity	NPC72211
0.784	Intermediate Similarity	NPC280799
0.7814	Intermediate Similarity	NPC97746
0.7804	Intermediate Similarity	NPC16352
0.7804	Intermediate Similarity	NPC220851
0.7804	Intermediate Similarity	NPC144452
0.7797	Intermediate Similarity	NPC473188
0.7778	Intermediate Similarity	NPC83111
0.7766	Intermediate Similarity	NPC46580
0.7761	Intermediate Similarity	NPC70259
0.7756	Intermediate Similarity	NPC165599
0.7733	Intermediate Similarity	NPC160898
0.7729	Intermediate Similarity	NPC321428
0.7727	Intermediate Similarity	NPC128751
0.7714	Intermediate Similarity	NPC219087
0.7714	Intermediate Similarity	NPC48353
0.7711	Intermediate Similarity	NPC43787
0.7711	Intermediate Similarity	NPC205934
0.7696	Intermediate Similarity	NPC213308
0.7688	Intermediate Similarity	NPC106833
0.7688	Intermediate Similarity	NPC469497
0.767	Intermediate Similarity	NPC162484
0.7665	Intermediate Similarity	NPC241025
0.7644	Intermediate Similarity	NPC244741
0.7636	Intermediate Similarity	NPC474688
0.7635	Intermediate Similarity	NPC141454
0.7628	Intermediate Similarity	NPC276657
0.7626	Intermediate Similarity	NPC194740
0.7621	Intermediate Similarity	NPC199277
0.7621	Intermediate Similarity	NPC135887
0.7606	Intermediate Similarity	NPC74969
0.7606	Intermediate Similarity	NPC322064
0.7606	Intermediate Similarity	NPC469928
0.76	Intermediate Similarity	NPC475844
0.7585	Intermediate Similarity	NPC476098
0.7581	Intermediate Similarity	NPC473179
0.7581	Intermediate Similarity	NPC298436
0.7561	Intermediate Similarity	NPC128823
0.755	Intermediate Similarity	NPC221873
0.7547	Intermediate Similarity	NPC294620
0.7538	Intermediate Similarity	NPC96890
0.7535	Intermediate Similarity	NPC303658
0.7535	Intermediate Similarity	NPC473041
0.7534	Intermediate Similarity	NPC39370
0.7526	Intermediate Similarity	NPC303225
0.7525	Intermediate Similarity	NPC84478
0.7523	Intermediate Similarity	NPC473186
0.7523	Intermediate Similarity	NPC152768
0.7523	Intermediate Similarity	NPC148183
0.7512	Intermediate Similarity	NPC477532
0.7512	Intermediate Similarity	NPC60621
0.7512	Intermediate Similarity	NPC472284
0.75	Intermediate Similarity	NPC146418
0.7488	Intermediate Similarity	NPC267423
0.7488	Intermediate Similarity	NPC476044
0.7488	Intermediate Similarity	NPC209769
0.7488	Intermediate Similarity	NPC27041
0.7478	Intermediate Similarity	NPC91868
0.7478	Intermediate Similarity	NPC63971
0.7476	Intermediate Similarity	NPC88008
0.7476	Intermediate Similarity	NPC53344
0.7467	Intermediate Similarity	NPC469734
0.7466	Intermediate Similarity	NPC471762
0.7453	Intermediate Similarity	NPC269367
0.745	Intermediate Similarity	NPC194040
0.7443	Intermediate Similarity	NPC122436
0.744	Intermediate Similarity	NPC315491
0.744	Intermediate Similarity	NPC45459
0.7438	Intermediate Similarity	NPC99666
0.743	Intermediate Similarity	NPC89508
0.743	Intermediate Similarity	NPC31700
0.7429	Intermediate Similarity	NPC175602
0.7424	Intermediate Similarity	NPC78609
0.7419	Intermediate Similarity	NPC74360
0.7415	Intermediate Similarity	NPC242209
0.7406	Intermediate Similarity	NPC201697
0.7391	Intermediate Similarity	NPC178858
0.7383	Intermediate Similarity	NPC110182
0.7371	Intermediate Similarity	NPC309845
0.7371	Intermediate Similarity	NPC11464
0.7361	Intermediate Similarity	NPC183407
0.7358	Intermediate Similarity	NPC475910
0.7342	Intermediate Similarity	NPC473185
0.7336	Intermediate Similarity	NPC220337
0.7333	Intermediate Similarity	NPC473105
0.733	Intermediate Similarity	NPC21638
0.733	Intermediate Similarity	NPC476818
0.7327	Intermediate Similarity	NPC305984
0.7327	Intermediate Similarity	NPC312645
0.7327	Intermediate Similarity	NPC472285
0.7327	Intermediate Similarity	NPC206186
0.7324	Intermediate Similarity	NPC61038
0.7321	Intermediate Similarity	NPC471944
0.7321	Intermediate Similarity	NPC14288
0.7321	Intermediate Similarity	NPC477112
0.7315	Intermediate Similarity	NPC16066
0.7309	Intermediate Similarity	NPC252251
0.7309	Intermediate Similarity	NPC66777
0.7302	Intermediate Similarity	NPC264176
0.7299	Intermediate Similarity	NPC470930
0.7297	Intermediate Similarity	NPC214142
0.7297	Intermediate Similarity	NPC319232
0.7297	Intermediate Similarity	NPC24370
0.7291	Intermediate Similarity	NPC242928
0.7286	Intermediate Similarity	NPC478032
0.7282	Intermediate Similarity	NPC326634
0.7281	Intermediate Similarity	NPC470784
0.7277	Intermediate Similarity	NPC470931
0.7273	Intermediate Similarity	NPC329747
0.7269	Intermediate Similarity	NPC477549
0.7268	Intermediate Similarity	NPC67551
0.7265	Intermediate Similarity	NPC34580
0.7265	Intermediate Similarity	NPC261251
0.7265	Intermediate Similarity	NPC118559
0.7265	Intermediate Similarity	NPC304307
0.7265	Intermediate Similarity	NPC124920
0.7264	Intermediate Similarity	NPC472286
0.7264	Intermediate Similarity	NPC472287
0.726	Intermediate Similarity	NPC269270
0.7257	Intermediate Similarity	NPC284888
0.7255	Intermediate Similarity	NPC154339
0.7251	Intermediate Similarity	NPC223427
0.7251	Intermediate Similarity	NPC53144
0.7244	Intermediate Similarity	NPC119006
0.7244	Intermediate Similarity	NPC260434
0.7244	Intermediate Similarity	NPC477531
0.7241	Intermediate Similarity	NPC278434
0.7237	Intermediate Similarity	NPC15801
0.7237	Intermediate Similarity	NPC184680
0.7237	Intermediate Similarity	NPC235685
0.7232	Intermediate Similarity	NPC100547
0.7228	Intermediate Similarity	NPC314002
0.7227	Intermediate Similarity	NPC14686
0.7225	Intermediate Similarity	NPC280714
0.7217	Intermediate Similarity	NPC132539

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 NPC86834 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	688
0.2-0.3	937
0.3-0.4	1515
0.4-0.5	3095
0.5-0.6	1910
0.6-0.7	610
0.7-0.8	51
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7805	Intermediate Similarity	NPD5901	Discontinued
0.7778	Intermediate Similarity	NPD2916	Discontinued
0.7639	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD5632	Approved
0.7598	Intermediate Similarity	NPD3986	Discontinued
0.7525	Intermediate Similarity	NPD5937	Approved
0.7477	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD6790	Phase 1
0.744	Intermediate Similarity	NPD484	Approved
0.7413	Intermediate Similarity	NPD4948	Discontinued
0.7379	Intermediate Similarity	NPD5003	Discontinued
0.7371	Intermediate Similarity	NPD1326	Approved
0.7371	Intermediate Similarity	NPD1325	Approved
0.7295	Intermediate Similarity	NPD7948	Phase 1
0.7289	Intermediate Similarity	NPD3746	Discontinued
0.7277	Intermediate Similarity	NPD6376	Discontinued
0.7264	Intermediate Similarity	NPD3003	Approved
0.7255	Intermediate Similarity	NPD2564	Approved
0.7255	Intermediate Similarity	NPD2565	Phase 2
0.7249	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5488	Discontinued
0.7238	Intermediate Similarity	NPD4511	Phase 1
0.7231	Intermediate Similarity	NPD2844	Phase 3
0.7215	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD4312	Approved
0.7181	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4373	Phase 2
0.7168	Intermediate Similarity	NPD6962	Phase 2
0.715	Intermediate Similarity	NPD802	Phase 2
0.715	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD6242	Discontinued
0.7143	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD5151	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4952	Phase 3
0.7124	Intermediate Similarity	NPD5479	Discontinued
0.7111	Intermediate Similarity	NPD3259	Approved
0.7111	Intermediate Similarity	NPD4845	Discontinued
0.711	Intermediate Similarity	NPD3243	Approved
0.7109	Intermediate Similarity	NPD4601	Approved
0.7109	Intermediate Similarity	NPD4600	Approved
0.7104	Intermediate Similarity	NPD3258	Approved
0.7097	Intermediate Similarity	NPD5416	Discontinued
0.7085	Intermediate Similarity	NPD6995	Phase 1
0.7081	Intermediate Similarity	NPD5512	Phase 3
0.7078	Intermediate Similarity	NPD7803	Approved
0.7076	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD5482	Discontinued
0.7062	Intermediate Similarity	NPD1768	Approved
0.704	Intermediate Similarity	NPD7181	Phase 3
0.7039	Intermediate Similarity	NPD1534	Approved
0.7037	Intermediate Similarity	NPD5658	Approved
0.703	Intermediate Similarity	NPD5445	Approved
0.7026	Intermediate Similarity	NPD4561	Discontinued
0.7014	Intermediate Similarity	NPD5164	Discontinued
0.7014	Intermediate Similarity	NPD2727	Phase 2
0.7012	Intermediate Similarity	NPD7955	Approved
0.7012	Intermediate Similarity	NPD7956	Approved
0.7	Intermediate Similarity	NPD5902	Approved
0.7	Intermediate Similarity	NPD3257	Approved
0.7	Intermediate Similarity	NPD5903	Approved
0.6996	Remote Similarity	NPD7417	Discontinued
0.6983	Remote Similarity	NPD6531	Approved
0.6983	Remote Similarity	NPD6530	Approved
0.6982	Remote Similarity	NPD7395	Discontinued
0.6982	Remote Similarity	NPD7878	Phase 2
0.6981	Remote Similarity	NPD8395	Approved
0.6981	Remote Similarity	NPD8396	Approved
0.696	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.696	Remote Similarity	NPD8428	Approved
0.696	Remote Similarity	NPD8465	Approved
0.696	Remote Similarity	NPD8467	Approved
0.696	Remote Similarity	NPD8427	Approved
0.696	Remote Similarity	NPD8466	Approved
0.696	Remote Similarity	NPD8429	Approved
0.6947	Remote Similarity	NPD3925	Approved
0.6944	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1505	Phase 2
0.6941	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4506	Discontinued
0.6923	Remote Similarity	NPD8363	Approved
0.6923	Remote Similarity	NPD8364	Approved
0.6917	Remote Similarity	NPD8460	Approved
0.6917	Remote Similarity	NPD8459	Approved
0.6916	Remote Similarity	NPD7603	Discontinued
0.6914	Remote Similarity	NPD7708	Approved
0.6909	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3814	Phase 1
0.6897	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5612	Discontinued
0.6886	Remote Similarity	NPD4328	Approved
0.6867	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6176	Phase 1
0.6852	Remote Similarity	NPD2920	Discontinued
0.685	Remote Similarity	NPD8425	Approved
0.685	Remote Similarity	NPD8426	Approved
0.6845	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5429	Discontinued
0.6835	Remote Similarity	NPD1392	Approved
0.6833	Remote Similarity	NPD3330	Phase 1
0.6832	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD482	Approved
0.683	Remote Similarity	NPD6985	Discontinued
0.6825	Remote Similarity	NPD1038	Approved
0.6822	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.682	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.682	Remote Similarity	NPD6987	Phase 1
0.682	Remote Similarity	NPD5426	Phase 3
0.6814	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7558	Phase 2
0.68	Remote Similarity	NPD7194	Discontinued
0.68	Remote Similarity	NPD1921	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD5936	Approved
0.6787	Remote Similarity	NPD5939	Approved
0.6774	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5293	Phase 2
0.6767	Remote Similarity	NPD4885	Approved
0.6762	Remote Similarity	NPD8091	Phase 3
0.6762	Remote Similarity	NPD4499	Approved
0.6761	Remote Similarity	NPD6456	Discontinued
0.6758	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7069	Discontinued
0.6757	Remote Similarity	NPD2794	Discontinued
0.6751	Remote Similarity	NPD6716	Phase 1
0.6746	Remote Similarity	NPD2383	Phase 1
0.6744	Remote Similarity	NPD2176	Approved
0.6744	Remote Similarity	NPD2175	Phase 3
0.6744	Remote Similarity	NPD2177	Approved
0.6743	Remote Similarity	NPD3947	Discontinued
0.6742	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7994	Phase 2
0.6734	Remote Similarity	NPD5450	Discontinued
0.6727	Remote Similarity	NPD2510	Approved
0.6727	Remote Similarity	NPD2509	Approved
0.6726	Remote Similarity	NPD6770	Approved
0.6724	Remote Similarity	NPD1867	Approved
0.6723	Remote Similarity	NPD5805	Approved
0.672	Remote Similarity	NPD9277	Approved
0.672	Remote Similarity	NPD75	Approved
0.6713	Remote Similarity	NPD4500	Approved
0.6713	Remote Similarity	NPD4501	Approved
0.6712	Remote Similarity	NPD7470	Discontinued
0.6712	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD7001	Phase 3
0.6699	Remote Similarity	NPD5473	Discontinued
0.6698	Remote Similarity	NPD7946	Pre-registration
0.6698	Remote Similarity	NPD7777	Approved
0.6698	Remote Similarity	NPD7778	Approved
0.6698	Remote Similarity	NPD53	Approved
0.6684	Remote Similarity	NPD1592	Phase 3
0.6683	Remote Similarity	NPD1685	Approved
0.6683	Remote Similarity	NPD1684	Approved
0.6683	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD7222	Phase 2
0.6682	Remote Similarity	NPD7452	Approved
0.6682	Remote Similarity	NPD7453	Approved
0.6681	Remote Similarity	NPD7853	Phase 2
0.6667	Remote Similarity	NPD9274	Approved
0.6667	Remote Similarity	NPD3178	Discontinued
0.6667	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5065	Approved
0.6667	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9276	Approved
0.6667	Remote Similarity	NPD7689	Approved
0.6667	Remote Similarity	NPD9275	Approved
0.6667	Remote Similarity	NPD9278	Suspended
0.6667	Remote Similarity	NPD5637	Discontinued
0.6667	Remote Similarity	NPD4539	Phase 1
0.6653	Remote Similarity	NPD3809	Discontinued
0.6652	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD7688	Phase 1
0.6651	Remote Similarity	NPD6975	Discontinued
0.6651	Remote Similarity	NPD5913	Phase 3
0.6651	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.665	Remote Similarity	NPD1631	Approved
0.6639	Remote Similarity	NPD8358	Approved
0.6637	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD5067	Phase 2
0.6637	Remote Similarity	NPD5066	Phase 2
0.6636	Remote Similarity	NPD4418	Discontinued
0.6636	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD2092	Phase 2
0.6635	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD2095	Phase 2
0.6635	Remote Similarity	NPD2094	Phase 2
0.6622	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD7538	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