NPASS Compound

Structure

CID209769 OpenBabel06191716002D 21 24 0 0 0 0 0 0 0 0999 V2000 -0.0316 -1.9456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5056 1.8387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0109 0.9633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8418 -1.4453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0075 -1.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8417 -0.4813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6686 0.9636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8342 1.4452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6688 -1.9273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8345 -1.4456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1727 -1.4454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6687 0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5036 -1.4455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0074 0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5035 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1726 -0.4814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8344 -0.4816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0001 0.9634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3378 0.0003 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.0075 1.0004 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 11 1 0 0 0 0 6 14 2 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 13 2 0 0 0 0 10 17 2 0 0 0 0 11 13 1 0 0 0 0 11 16 2 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 14 20 1 0 0 0 0 15 19 1 0 0 0 0 16 19 1 0 0 0 0 17 21 1 0 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1044.55
Volume:	1004.341
LogP:	2.706
LogD:	2.487
LogS:	-3.553
# Rotatable Bonds:	10
TPSA:	314.83
# H-Bond Aceptor:	21
# H-Bond Donor:	11
# Rings:	10
# Heavy Atoms:	21

MedChem Properties

QED Drug-Likeness Score:	0.097
Synthetic Accessibility Score:	6.838
Fsp3:	0.962
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.034
MDCK Permeability:	0.00012028028868371621
Pgp-inhibitor:	0.866
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.966
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	70.1268081665039%
Volume Distribution (VD):	-0.162
Pgp-substrate:	11.848018646240234%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.969
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.227
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.052
CYP3A4-inhibitor:	0.13
CYP3A4-substrate:	0.019

ADMET: Excretion

Clearance (CL):	0.036
Half-life (T1/2):	0.733

ADMET: Toxicity

hERG Blockers:	0.209
Human Hepatotoxicity (H-HT):	0.208
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.095
Rat Oral Acute Toxicity:	0.136
Maximum Recommended Daily Dose:	0.468
Skin Sensitization:	0.903
Carcinogencity:	0.006
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.843

Download Data

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

Natural Product: NPC209769

Natural Product ID:	NPC209769
*Common Name:**	Claurailas B
IUPAC Name:	3,3,5-trimethyl-11H-pyrano[3,2-a]carbazol-10-ol
Synonyms:	Claurailas B
Standard InCHIKey:	DOPPWRJNMKMWAZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H17NO2/c1-10-9-13-11-5-4-6-14(20)16(11)19-15(13)12-7-8-18(2,3)21-17(10)12/h4-9,19-20H,1-3H3
SMILES:	Cc1cc2c3cccc(c3[nH]c2c2C=CC(C)(C)Oc12)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1689796
PubChem CID:	51039826
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
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]
NPO21978	Clausena harmandiana	Species	Rutaceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3236015]
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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	>	200000.0	nM	PMID[469314]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	200000.0	nM	PMID[469314]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	200000.0	nM	PMID[469314]

☑ 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 NPC209769 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	593
0.1-0.2	3852
0.2-0.3	13547
0.3-0.4	4209
0.4-0.5	14701
0.5-0.6	4162
0.6-0.7	1295
0.7-0.8	266
0.8-0.85	34
0.85-0.9	29
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9572	High Similarity	NPC470930
0.9259	High Similarity	NPC475112
0.9259	High Similarity	NPC291535
0.9259	High Similarity	NPC475085
0.9031	High Similarity	NPC48353
0.895	High Similarity	NPC473179
0.8947	High Similarity	NPC72211
0.8942	High Similarity	NPC70259
0.8918	High Similarity	NPC476106
0.8912	High Similarity	NPC162484
0.8895	High Similarity	NPC243834
0.8895	High Similarity	NPC70956
0.8889	High Similarity	NPC43787
0.8889	High Similarity	NPC205934
0.878	High Similarity	NPC202503
0.8687	High Similarity	NPC201697
0.868	High Similarity	NPC193777
0.8647	High Similarity	NPC473185
0.8615	High Similarity	NPC267423
0.8608	High Similarity	NPC128823
0.8542	High Similarity	NPC475190
0.8524	High Similarity	NPC475253
0.852	High Similarity	NPC476044
0.8503	High Similarity	NPC474798
0.8497	Intermediate Similarity	NPC131017
0.8495	Intermediate Similarity	NPC477532
0.8466	Intermediate Similarity	NPC94943
0.845	Intermediate Similarity	NPC470931
0.8443	Intermediate Similarity	NPC473182
0.8429	Intermediate Similarity	NPC252251
0.8429	Intermediate Similarity	NPC242928
0.8413	Intermediate Similarity	NPC190007
0.839	Intermediate Similarity	NPC314552
0.8389	Intermediate Similarity	NPC209174
0.8373	Intermediate Similarity	NPC179287
0.836	Intermediate Similarity	NPC212535
0.8349	Intermediate Similarity	NPC477531
0.8326	Intermediate Similarity	NPC473183
0.8318	Intermediate Similarity	NPC473184
0.8316	Intermediate Similarity	NPC153042
0.8233	Intermediate Similarity	NPC277351
0.8186	Intermediate Similarity	NPC199667
0.8186	Intermediate Similarity	NPC11464
0.8137	Intermediate Similarity	NPC473181
0.8109	Intermediate Similarity	NPC135887
0.8109	Intermediate Similarity	NPC199277
0.8107	Intermediate Similarity	NPC473180
0.81	Intermediate Similarity	NPC11017
0.8095	Intermediate Similarity	NPC132642
0.8095	Intermediate Similarity	NPC477533
0.8073	Intermediate Similarity	NPC6786
0.8057	Intermediate Similarity	NPC198503
0.8048	Intermediate Similarity	NPC208084
0.8019	Intermediate Similarity	NPC94157
0.8009	Intermediate Similarity	NPC150239
0.798	Intermediate Similarity	NPC223427
0.7959	Intermediate Similarity	NPC246700
0.7938	Intermediate Similarity	NPC84478
0.792	Intermediate Similarity	NPC473188
0.7917	Intermediate Similarity	NPC274640
0.7917	Intermediate Similarity	NPC88363
0.7915	Intermediate Similarity	NPC184408
0.7915	Intermediate Similarity	NPC247803
0.7897	Intermediate Similarity	NPC51388
0.7895	Intermediate Similarity	NPC474409
0.7885	Intermediate Similarity	NPC87413
0.7857	Intermediate Similarity	NPC118228
0.7847	Intermediate Similarity	NPC203168
0.7843	Intermediate Similarity	NPC66815
0.7837	Intermediate Similarity	NPC219664
0.7833	Intermediate Similarity	NPC329747
0.7826	Intermediate Similarity	NPC475910
0.7824	Intermediate Similarity	NPC72980
0.7824	Intermediate Similarity	NPC200888
0.782	Intermediate Similarity	NPC470799
0.782	Intermediate Similarity	NPC8022
0.7784	Intermediate Similarity	NPC478032
0.7778	Intermediate Similarity	NPC128751
0.7767	Intermediate Similarity	NPC144452
0.7763	Intermediate Similarity	NPC474701
0.7757	Intermediate Similarity	NPC174760
0.7757	Intermediate Similarity	NPC225279
0.774	Intermediate Similarity	NPC39679
0.7739	Intermediate Similarity	NPC469497
0.7739	Intermediate Similarity	NPC106833
0.7729	Intermediate Similarity	NPC304183
0.7725	Intermediate Similarity	NPC471080
0.7725	Intermediate Similarity	NPC39500
0.7725	Intermediate Similarity	NPC469592
0.7723	Intermediate Similarity	NPC475844
0.7721	Intermediate Similarity	NPC280799
0.7716	Intermediate Similarity	NPC42591
0.7714	Intermediate Similarity	NPC187501
0.7713	Intermediate Similarity	NPC131486
0.77	Intermediate Similarity	NPC293151
0.7692	Intermediate Similarity	NPC249583
0.7692	Intermediate Similarity	NPC4687
0.7682	Intermediate Similarity	NPC474688
0.7681	Intermediate Similarity	NPC285558
0.7678	Intermediate Similarity	NPC310211
0.7678	Intermediate Similarity	NPC308137
0.7664	Intermediate Similarity	NPC46561
0.7664	Intermediate Similarity	NPC469594
0.7662	Intermediate Similarity	NPC280964
0.7662	Intermediate Similarity	NPC114335
0.7662	Intermediate Similarity	NPC141915
0.7653	Intermediate Similarity	NPC3207
0.7638	Intermediate Similarity	NPC66083
0.763	Intermediate Similarity	NPC23294
0.7629	Intermediate Similarity	NPC288943
0.7628	Intermediate Similarity	NPC148409
0.7623	Intermediate Similarity	NPC473187
0.7617	Intermediate Similarity	NPC169402
0.7614	Intermediate Similarity	NPC176127
0.761	Intermediate Similarity	NPC18487
0.7608	Intermediate Similarity	NPC283117
0.7606	Intermediate Similarity	NPC116238
0.7594	Intermediate Similarity	NPC26679
0.7583	Intermediate Similarity	NPC303951
0.7576	Intermediate Similarity	NPC189079
0.757	Intermediate Similarity	NPC170114
0.7559	Intermediate Similarity	NPC478074
0.7548	Intermediate Similarity	NPC475774
0.7547	Intermediate Similarity	NPC294375
0.7546	Intermediate Similarity	NPC193267
0.7546	Intermediate Similarity	NPC213530
0.7536	Intermediate Similarity	NPC185782
0.7532	Intermediate Similarity	NPC133609
0.7523	Intermediate Similarity	NPC470549
0.7512	Intermediate Similarity	NPC164374
0.7512	Intermediate Similarity	NPC137929
0.7512	Intermediate Similarity	NPC316981
0.7512	Intermediate Similarity	NPC110741
0.75	Intermediate Similarity	NPC314573
0.75	Intermediate Similarity	NPC61350
0.75	Intermediate Similarity	NPC283152
0.75	Intermediate Similarity	NPC303658
0.7488	Intermediate Similarity	NPC86834
0.7488	Intermediate Similarity	NPC210828
0.7477	Intermediate Similarity	NPC266931
0.7477	Intermediate Similarity	NPC476287
0.7464	Intermediate Similarity	NPC245816
0.7464	Intermediate Similarity	NPC469440
0.7464	Intermediate Similarity	NPC476138
0.7452	Intermediate Similarity	NPC470586
0.744	Intermediate Similarity	NPC476167
0.7431	Intermediate Similarity	NPC86078
0.7404	Intermediate Similarity	NPC329793
0.7402	Intermediate Similarity	NPC99666
0.74	Intermediate Similarity	NPC62069
0.7396	Intermediate Similarity	NPC118511
0.7393	Intermediate Similarity	NPC45190
0.7393	Intermediate Similarity	NPC300156
0.7391	Intermediate Similarity	NPC306376
0.7391	Intermediate Similarity	NPC192315
0.7383	Intermediate Similarity	NPC208284
0.7379	Intermediate Similarity	NPC251090
0.7376	Intermediate Similarity	NPC46580
0.7371	Intermediate Similarity	NPC469589
0.7368	Intermediate Similarity	NPC232727
0.7366	Intermediate Similarity	NPC307963
0.7364	Intermediate Similarity	NPC280272
0.7353	Intermediate Similarity	NPC469390
0.7349	Intermediate Similarity	NPC294620
0.7345	Intermediate Similarity	NPC39370
0.7339	Intermediate Similarity	NPC473041
0.7336	Intermediate Similarity	NPC167860
0.7336	Intermediate Similarity	NPC123976
0.7333	Intermediate Similarity	NPC473186
0.7327	Intermediate Similarity	NPC183407
0.7327	Intermediate Similarity	NPC204385
0.7324	Intermediate Similarity	NPC477111
0.7319	Intermediate Similarity	NPC244543
0.7318	Intermediate Similarity	NPC310118
0.731	Intermediate Similarity	NPC312872
0.7302	Intermediate Similarity	NPC9894
0.7295	Intermediate Similarity	NPC13880
0.7277	Intermediate Similarity	NPC26850
0.7265	Intermediate Similarity	NPC227908
0.7257	Intermediate Similarity	NPC469554
0.7256	Intermediate Similarity	NPC471304
0.7251	Intermediate Similarity	NPC470678
0.7248	Intermediate Similarity	NPC330009
0.722	Intermediate Similarity	NPC76748
0.7217	Intermediate Similarity	NPC477861
0.7214	Intermediate Similarity	NPC118776
0.7207	Intermediate Similarity	NPC118121
0.72	Intermediate Similarity	NPC476997
0.72	Intermediate Similarity	NPC194740
0.7198	Intermediate Similarity	NPC279401
0.7198	Intermediate Similarity	NPC79293
0.7196	Intermediate Similarity	NPC321428
0.7192	Intermediate Similarity	NPC473189
0.7184	Intermediate Similarity	NPC92111
0.7182	Intermediate Similarity	NPC173080
0.7181	Intermediate Similarity	NPC101543
0.7176	Intermediate Similarity	NPC5145
0.7175	Intermediate Similarity	NPC205372
0.7175	Intermediate Similarity	NPC211416
0.7174	Intermediate Similarity	NPC11408

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 NPC209769 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	363
0.1-0.2	729
0.2-0.3	897
0.3-0.4	1598
0.4-0.5	2868
0.5-0.6	2002
0.6-0.7	617
0.7-0.8	74
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.839	Intermediate Similarity	NPD5164	Discontinued
0.8079	Intermediate Similarity	NPD3003	Approved
0.7857	Intermediate Similarity	NPD5902	Approved
0.7857	Intermediate Similarity	NPD5903	Approved
0.7783	Intermediate Similarity	NPD1768	Approved
0.7778	Intermediate Similarity	NPD7453	Approved
0.7778	Intermediate Similarity	NPD7222	Phase 2
0.7778	Intermediate Similarity	NPD7452	Approved
0.7755	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD5658	Approved
0.7736	Intermediate Similarity	NPD5612	Discontinued
0.7714	Intermediate Similarity	NPD4502	Phase 2
0.7685	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD7558	Phase 2
0.7581	Intermediate Similarity	NPD6985	Discontinued
0.7546	Intermediate Similarity	NPD7194	Discontinued
0.7524	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD1392	Approved
0.75	Intermediate Similarity	NPD4418	Discontinued
0.75	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD4511	Phase 1
0.7415	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD6590	Discontinued
0.7385	Intermediate Similarity	NPD3875	Discontinued
0.7383	Intermediate Similarity	NPD5067	Phase 2
0.7383	Intermediate Similarity	NPD5066	Phase 2
0.7383	Intermediate Similarity	NPD5936	Approved
0.7383	Intermediate Similarity	NPD5939	Approved
0.7383	Intermediate Similarity	NPD6220	Phase 3
0.7379	Intermediate Similarity	NPD5512	Phase 3
0.7366	Intermediate Similarity	NPD1038	Approved
0.7358	Intermediate Similarity	NPD5429	Discontinued
0.7339	Intermediate Similarity	NPD5632	Approved
0.7327	Intermediate Similarity	NPD5256	Discontinued
0.7313	Intermediate Similarity	NPD4454	Phase 2
0.7304	Intermediate Similarity	NPD2565	Phase 2
0.7304	Intermediate Similarity	NPD2564	Approved
0.7282	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD6290	Phase 2
0.7273	Intermediate Similarity	NPD2175	Phase 3
0.7273	Intermediate Similarity	NPD2177	Approved
0.7273	Intermediate Similarity	NPD2176	Approved
0.726	Intermediate Similarity	NPD7948	Phase 1
0.7246	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD5530	Phase 1
0.7225	Intermediate Similarity	NPD6494	Phase 2
0.7212	Intermediate Similarity	NPD1505	Phase 2
0.72	Intermediate Similarity	NPD3920	Phase 2
0.719	Intermediate Similarity	NPD3825	Phase 3
0.7185	Intermediate Similarity	NPD8244	Phase 2
0.7184	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5913	Phase 3
0.7177	Intermediate Similarity	NPD5003	Discontinued
0.7172	Intermediate Similarity	NPD8364	Approved
0.7172	Intermediate Similarity	NPD8363	Approved
0.7157	Intermediate Similarity	NPD1325	Approved
0.7157	Intermediate Similarity	NPD1326	Approved
0.7157	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD8403	Phase 1
0.715	Intermediate Similarity	NPD6159	Phase 2
0.7129	Intermediate Similarity	NPD4203	Approved
0.7129	Intermediate Similarity	NPD4204	Approved
0.7117	Intermediate Similarity	NPD5930	Phase 3
0.7114	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7069	Discontinued
0.7105	Intermediate Similarity	NPD3746	Discontinued
0.7095	Intermediate Similarity	NPD6988	Phase 1
0.709	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6569	Phase 2
0.7059	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5559	Phase 2
0.7048	Intermediate Similarity	NPD6550	Discontinued
0.7043	Intermediate Similarity	NPD2951	Discontinued
0.7035	Intermediate Similarity	NPD7603	Discontinued
0.7032	Intermediate Similarity	NPD6202	Discontinued
0.7028	Intermediate Similarity	NPD8396	Approved
0.7028	Intermediate Similarity	NPD8395	Approved
0.7027	Intermediate Similarity	NPD7395	Discontinued
0.7027	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6643	Discontinued
0.7014	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6473	Phase 1
0.7	Intermediate Similarity	NPD8465	Approved
0.7	Intermediate Similarity	NPD8428	Approved
0.7	Intermediate Similarity	NPD8429	Approved
0.7	Intermediate Similarity	NPD8427	Approved
0.7	Intermediate Similarity	NPD8467	Approved
0.7	Intermediate Similarity	NPD8466	Approved
0.6996	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3963	Phase 1
0.6974	Remote Similarity	NPD7555	Discontinued
0.6972	Remote Similarity	NPD4437	Phase 3
0.696	Remote Similarity	NPD3263	Phase 3
0.696	Remote Similarity	NPD1273	Discontinued
0.6952	Remote Similarity	NPD802	Phase 2
0.6949	Remote Similarity	NPD4349	Approved
0.6949	Remote Similarity	NPD4350	Approved
0.6948	Remote Similarity	NPD3814	Phase 1
0.6948	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD2916	Discontinued
0.692	Remote Similarity	NPD3763	Approved
0.6916	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6962	Phase 2
0.6909	Remote Similarity	NPD5416	Discontinued
0.6907	Remote Similarity	NPD5617	Suspended
0.6904	Remote Similarity	NPD5482	Discontinued
0.6903	Remote Similarity	NPD6736	Discontinued
0.69	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD6324	Phase 1
0.6898	Remote Similarity	NPD2920	Discontinued
0.6892	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.689	Remote Similarity	NPD8425	Approved
0.689	Remote Similarity	NPD8459	Approved
0.689	Remote Similarity	NPD8426	Approved
0.689	Remote Similarity	NPD8460	Approved
0.689	Remote Similarity	NPD3342	Phase 2
0.6889	Remote Similarity	NPD6242	Discontinued
0.6889	Remote Similarity	NPD7678	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD3816	Phase 1
0.6878	Remote Similarity	NPD3815	Phase 1
0.6878	Remote Similarity	NPD3330	Phase 1
0.6866	Remote Similarity	NPD4795	Phase 2
0.6863	Remote Similarity	NPD7479	Phase 2
0.686	Remote Similarity	NPD2762	Phase 2
0.6856	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4605	Approved
0.6854	Remote Similarity	NPD4604	Approved
0.6846	Remote Similarity	NPD6743	Phase 2
0.6846	Remote Similarity	NPD6742	Phase 2
0.6845	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD3402	Phase 1
0.6842	Remote Similarity	NPD6246	Approved
0.684	Remote Similarity	NPD6251	Discontinued
0.684	Remote Similarity	NPD1867	Approved
0.6835	Remote Similarity	NPD6150	Discontinued
0.6833	Remote Similarity	NPD3986	Discontinued
0.6828	Remote Similarity	NPD1954	Phase 1
0.6828	Remote Similarity	NPD7219	Approved
0.6828	Remote Similarity	NPD7221	Approved
0.6825	Remote Similarity	NPD3921	Approved
0.6825	Remote Similarity	NPD3923	Approved
0.6825	Remote Similarity	NPD3922	Approved
0.6825	Remote Similarity	NPD3924	Approved
0.6822	Remote Similarity	NPD7417	Discontinued
0.6807	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4927	Discontinued
0.6802	Remote Similarity	NPD2794	Discontinued
0.68	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD983	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5479	Discontinued
0.6797	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5022	Discontinued
0.6795	Remote Similarity	NPD3006	Discontinued
0.6794	Remote Similarity	NPD2749	Discontinued
0.6792	Remote Similarity	NPD6361	Phase 2
0.6789	Remote Similarity	NPD3397	Phase 2
0.6789	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7726	Phase 1
0.6783	Remote Similarity	NPD3259	Approved
0.6783	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD4373	Phase 2
0.678	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD4889	Approved
0.6777	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD7672	Approved
0.6773	Remote Similarity	NPD2189	Approved
0.6773	Remote Similarity	NPD2187	Approved
0.6773	Remote Similarity	NPD7671	Approved
0.6771	Remote Similarity	NPD5945	Phase 1
0.6771	Remote Similarity	NPD5944	Phase 1
0.6769	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4354	Approved
0.6765	Remote Similarity	NPD7413	Phase 3
0.6763	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1739	Approved
0.6759	Remote Similarity	NPD1740	Approved
0.6758	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD3842	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6340	Approved
0.6746	Remote Similarity	NPD6339	Approved
0.6744	Remote Similarity	NPD2727	Phase 2
0.6743	Remote Similarity	NPD6991	Approved
0.6739	Remote Similarity	NPD7675	Phase 3
0.6739	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7674	Phase 3
0.6739	Remote Similarity	NPD7426	Phase 1
0.6738	Remote Similarity	NPD4885	Approved
0.6732	Remote Similarity	NPD5751	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