NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	215.09
Volume:	223.13
LogP:	1.837
LogD:	1.592
LogS:	-3.037
# Rotatable Bonds:	0
TPSA:	53.09
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.706
Synthetic Accessibility Score:	3.223
Fsp3:	0.308
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.754
MDCK Permeability:	1.478259582654573e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.973
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.829
Plasma Protein Binding (PPB):	72.9073257446289%
Volume Distribution (VD):	0.945
Pgp-substrate:	27.94654083251953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.286
CYP1A2-substrate:	0.823
CYP2C19-inhibitor:	0.198
CYP2C19-substrate:	0.848
CYP2C9-inhibitor:	0.093
CYP2C9-substrate:	0.912
CYP2D6-inhibitor:	0.141
CYP2D6-substrate:	0.766
CYP3A4-inhibitor:	0.048
CYP3A4-substrate:	0.759

ADMET: Excretion

Clearance (CL):	3.192
Half-life (T1/2):	0.891

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.234
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.466
Rat Oral Acute Toxicity:	0.962
Maximum Recommended Daily Dose:	0.197
Skin Sensitization:	0.193
Carcinogencity:	0.263
Eye Corrosion:	0.004
Eye Irritation:	0.186
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC67551

Natural Product ID:	NPC67551
*Common Name:**	Bruceolline J
IUPAC Name:	(2R)-2-hydroxy-3,3-dimethyl-2,4-dihydrocyclopenta[b]indol-1-one
Synonyms:	Bruceolline J
Standard InCHIKey:	QLFDLIVQYIHVGJ-LBPRGKRZSA-N
Standard InCHI:	InChI=1S/C13H13NO2/c1-13(2)11-9(10(15)12(13)16)7-5-3-4-6-8(7)14-11/h3-6,12,14,16H,1-2H3/t12-/m0/s1
SMILES:	CC1(C)c2c(c3ccccc3[nH]2)C(=O)[C@@H]1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1922991
PubChem CID:	56833858
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles

*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
NPO15436	Brucea mollis	Species	Simaroubaceae	Eukaryota	n.a.	stem	n.a.	PMID[22070654]
NPO15436	Brucea mollis	Species	Simaroubaceae	Eukaryota	stems	n.a.	n.a.	PMID[22070654]
NPO15436	Brucea mollis	Species	Simaroubaceae	Eukaryota	n.a.	stem	n.a.	PMID[24199564]
NPO15436	Brucea mollis	Species	Simaroubaceae	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	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[566937]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[566937]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[566937]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[566937]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[566937]

☑ 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 NPC67551 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	300
0.1-0.2	1819
0.2-0.3	10315
0.3-0.4	19969
0.4-0.5	6022
0.5-0.6	2255
0.6-0.7	1697
0.7-0.8	311
0.8-0.85	4
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9043	High Similarity	NPC12344
0.8854	High Similarity	NPC249428
0.8634	High Similarity	NPC267343
0.8571	High Similarity	NPC154339
0.8382	Intermediate Similarity	NPC214106
0.8325	Intermediate Similarity	NPC134848
0.7926	Intermediate Similarity	NPC221873
0.7914	Intermediate Similarity	NPC315555
0.79	Intermediate Similarity	NPC219087
0.7725	Intermediate Similarity	NPC99428
0.7688	Intermediate Similarity	NPC55772
0.7684	Intermediate Similarity	NPC278434
0.768	Intermediate Similarity	NPC115232
0.7677	Intermediate Similarity	NPC165599
0.7634	Intermediate Similarity	NPC111275
0.7614	Intermediate Similarity	NPC252338
0.7566	Intermediate Similarity	NPC469358
0.7565	Intermediate Similarity	NPC138370
0.7562	Intermediate Similarity	NPC244741
0.7551	Intermediate Similarity	NPC227582
0.7539	Intermediate Similarity	NPC160381
0.7525	Intermediate Similarity	NPC258062
0.7525	Intermediate Similarity	NPC171787
0.7513	Intermediate Similarity	NPC71037
0.7513	Intermediate Similarity	NPC195457
0.7513	Intermediate Similarity	NPC206967
0.7487	Intermediate Similarity	NPC81802
0.7487	Intermediate Similarity	NPC472210
0.7487	Intermediate Similarity	NPC247735
0.7487	Intermediate Similarity	NPC472295
0.7487	Intermediate Similarity	NPC269886
0.7475	Intermediate Similarity	NPC225821
0.7475	Intermediate Similarity	NPC183777
0.7473	Intermediate Similarity	NPC97525
0.7463	Intermediate Similarity	NPC87856
0.7459	Intermediate Similarity	NPC230869
0.7451	Intermediate Similarity	NPC187255
0.745	Intermediate Similarity	NPC260900
0.745	Intermediate Similarity	NPC123019
0.7444	Intermediate Similarity	NPC285469
0.744	Intermediate Similarity	NPC203614
0.744	Intermediate Similarity	NPC132211
0.7433	Intermediate Similarity	NPC472586
0.743	Intermediate Similarity	NPC268676
0.743	Intermediate Similarity	NPC27324
0.7427	Intermediate Similarity	NPC89508
0.7421	Intermediate Similarity	NPC302191
0.7413	Intermediate Similarity	NPC98715
0.7407	Intermediate Similarity	NPC472443
0.7405	Intermediate Similarity	NPC78020
0.7405	Intermediate Similarity	NPC154293
0.7402	Intermediate Similarity	NPC469743
0.7391	Intermediate Similarity	NPC42372
0.7382	Intermediate Similarity	NPC19679
0.738	Intermediate Similarity	NPC34508
0.7376	Intermediate Similarity	NPC477043
0.7376	Intermediate Similarity	NPC132539
0.7374	Intermediate Similarity	NPC141454
0.7373	Intermediate Similarity	NPC475619
0.7368	Intermediate Similarity	NPC198339
0.7366	Intermediate Similarity	NPC234999
0.736	Intermediate Similarity	NPC276517
0.7358	Intermediate Similarity	NPC147446
0.7356	Intermediate Similarity	NPC85702
0.7353	Intermediate Similarity	NPC127677
0.735	Intermediate Similarity	NPC214428
0.7347	Intermediate Similarity	NPC55493
0.7347	Intermediate Similarity	NPC472292
0.734	Intermediate Similarity	NPC293216
0.7337	Intermediate Similarity	NPC52557
0.7333	Intermediate Similarity	NPC472112
0.7333	Intermediate Similarity	NPC329858
0.7333	Intermediate Similarity	NPC74360
0.7333	Intermediate Similarity	NPC314333
0.733	Intermediate Similarity	NPC314394
0.7323	Intermediate Similarity	NPC472293
0.7323	Intermediate Similarity	NPC11445
0.7321	Intermediate Similarity	NPC312645
0.7317	Intermediate Similarity	NPC271862
0.7316	Intermediate Similarity	NPC219336
0.7308	Intermediate Similarity	NPC474412
0.7308	Intermediate Similarity	NPC76982
0.7304	Intermediate Similarity	NPC257175
0.7304	Intermediate Similarity	NPC46225
0.7302	Intermediate Similarity	NPC151635
0.7302	Intermediate Similarity	NPC267885
0.73	Intermediate Similarity	NPC74413
0.73	Intermediate Similarity	NPC241024
0.73	Intermediate Similarity	NPC472297
0.73	Intermediate Similarity	NPC472296
0.7295	Intermediate Similarity	NPC151976
0.7292	Intermediate Similarity	NPC472444
0.729	Intermediate Similarity	NPC112547
0.7283	Intermediate Similarity	NPC16667
0.7282	Intermediate Similarity	NPC303951
0.7277	Intermediate Similarity	NPC15840
0.7273	Intermediate Similarity	NPC471943
0.7273	Intermediate Similarity	NPC157828
0.7273	Intermediate Similarity	NPC204491
0.7273	Intermediate Similarity	NPC195239
0.7268	Intermediate Similarity	NPC86834
0.7268	Intermediate Similarity	NPC39679
0.7268	Intermediate Similarity	NPC210828
0.7263	Intermediate Similarity	NPC217372
0.7263	Intermediate Similarity	NPC15573
0.7263	Intermediate Similarity	NPC183662
0.726	Intermediate Similarity	NPC267965
0.7259	Intermediate Similarity	NPC472113
0.725	Intermediate Similarity	NPC131887
0.7249	Intermediate Similarity	NPC149155
0.7249	Intermediate Similarity	NPC203468
0.7249	Intermediate Similarity	NPC110500
0.7246	Intermediate Similarity	NPC9894
0.7246	Intermediate Similarity	NPC23294
0.7245	Intermediate Similarity	NPC83111
0.7243	Intermediate Similarity	NPC141428
0.7238	Intermediate Similarity	NPC472285
0.7234	Intermediate Similarity	NPC6982
0.7228	Intermediate Similarity	NPC300183
0.7225	Intermediate Similarity	NPC248041
0.7225	Intermediate Similarity	NPC126709
0.7225	Intermediate Similarity	NPC471284
0.7225	Intermediate Similarity	NPC213468
0.7225	Intermediate Similarity	NPC270009
0.722	Intermediate Similarity	NPC88008
0.7219	Intermediate Similarity	NPC317430
0.7217	Intermediate Similarity	NPC276657
0.7216	Intermediate Similarity	NPC163421
0.7216	Intermediate Similarity	NPC188387
0.7212	Intermediate Similarity	NPC473493
0.7212	Intermediate Similarity	NPC235900
0.7212	Intermediate Similarity	NPC475778
0.7211	Intermediate Similarity	NPC84347
0.7209	Intermediate Similarity	NPC267926
0.7204	Intermediate Similarity	NPC470508
0.7202	Intermediate Similarity	NPC159125
0.7198	Intermediate Similarity	NPC207726
0.7194	Intermediate Similarity	NPC175474
0.7192	Intermediate Similarity	NPC474116
0.7192	Intermediate Similarity	NPC162730
0.7188	Intermediate Similarity	NPC88110
0.7186	Intermediate Similarity	NPC85066
0.7186	Intermediate Similarity	NPC202812
0.7186	Intermediate Similarity	NPC181502
0.7183	Intermediate Similarity	NPC2395
0.7177	Intermediate Similarity	NPC472291
0.7176	Intermediate Similarity	NPC57690
0.7173	Intermediate Similarity	NPC293472
0.7173	Intermediate Similarity	NPC284775
0.7171	Intermediate Similarity	NPC18661
0.7171	Intermediate Similarity	NPC45190
0.7171	Intermediate Similarity	NPC277350
0.7169	Intermediate Similarity	NPC70155
0.7165	Intermediate Similarity	NPC165201
0.7164	Intermediate Similarity	NPC477044
0.7164	Intermediate Similarity	NPC477041
0.7164	Intermediate Similarity	NPC473747
0.7163	Intermediate Similarity	NPC235885
0.7163	Intermediate Similarity	NPC294375
0.7163	Intermediate Similarity	NPC87413
0.7158	Intermediate Similarity	NPC329688
0.7158	Intermediate Similarity	NPC189812
0.7151	Intermediate Similarity	NPC311276
0.7151	Intermediate Similarity	NPC102423
0.715	Intermediate Similarity	NPC470677
0.715	Intermediate Similarity	NPC192270
0.715	Intermediate Similarity	NPC231342
0.7143	Intermediate Similarity	NPC119700
0.7143	Intermediate Similarity	NPC471944
0.7136	Intermediate Similarity	NPC249583
0.7136	Intermediate Similarity	NPC321428
0.7136	Intermediate Similarity	NPC270918
0.7136	Intermediate Similarity	NPC283117
0.7135	Intermediate Similarity	NPC283219
0.7128	Intermediate Similarity	NPC282103
0.7122	Intermediate Similarity	NPC314648
0.7113	Intermediate Similarity	NPC139291
0.7113	Intermediate Similarity	NPC117027
0.7113	Intermediate Similarity	NPC472108
0.7108	Intermediate Similarity	NPC476874
0.7107	Intermediate Similarity	NPC34271
0.7105	Intermediate Similarity	NPC252572
0.7105	Intermediate Similarity	NPC472123
0.7098	Intermediate Similarity	NPC469896
0.7097	Intermediate Similarity	NPC242116
0.7095	Intermediate Similarity	NPC229348
0.7094	Intermediate Similarity	NPC475151
0.7094	Intermediate Similarity	NPC79129
0.7094	Intermediate Similarity	NPC249150
0.7094	Intermediate Similarity	NPC49196
0.7094	Intermediate Similarity	NPC313985
0.7094	Intermediate Similarity	NPC195461
0.7094	Intermediate Similarity	NPC213308
0.7094	Intermediate Similarity	NPC81654
0.7092	Intermediate Similarity	NPC62749
0.7092	Intermediate Similarity	NPC235684
0.709	Intermediate Similarity	NPC280548
0.7087	Intermediate Similarity	NPC471191
0.7087	Intermediate Similarity	NPC300156
0.7087	Intermediate Similarity	NPC82053

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 NPC67551 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	603
0.2-0.3	725
0.3-0.4	2180
0.4-0.5	3041
0.5-0.6	1890
0.6-0.7	435
0.7-0.8	44
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7596	Intermediate Similarity	NPD2844	Phase 3
0.744	Intermediate Similarity	NPD8160	Phase 2
0.7413	Intermediate Similarity	NPD6176	Phase 1
0.7402	Intermediate Similarity	NPD7941	Phase 3
0.7376	Intermediate Similarity	NPD6987	Phase 1
0.7374	Intermediate Similarity	NPD5003	Discontinued
0.7353	Intermediate Similarity	NPD2510	Approved
0.7353	Intermediate Similarity	NPD2509	Approved
0.734	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4499	Approved
0.7302	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD2091	Phase 2
0.7254	Intermediate Similarity	NPD2096	Phase 2
0.7249	Intermediate Similarity	NPD482	Approved
0.7245	Intermediate Similarity	NPD2565	Phase 2
0.7245	Intermediate Similarity	NPD2564	Approved
0.7233	Intermediate Similarity	NPD4506	Discontinued
0.7231	Intermediate Similarity	NPD4948	Discontinued
0.7216	Intermediate Similarity	NPD1592	Phase 3
0.7208	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2092	Phase 2
0.7202	Intermediate Similarity	NPD2095	Phase 2
0.7202	Intermediate Similarity	NPD2094	Phase 2
0.7194	Intermediate Similarity	NPD1534	Approved
0.7181	Intermediate Similarity	NPD1575	Approved
0.7181	Intermediate Similarity	NPD1573	Approved
0.7157	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1631	Approved
0.7123	Intermediate Similarity	NPD7878	Phase 2
0.7109	Intermediate Similarity	NPD3393	Approved
0.7109	Intermediate Similarity	NPD3389	Approved
0.7109	Intermediate Similarity	NPD3394	Approved
0.7094	Intermediate Similarity	NPD4601	Approved
0.7094	Intermediate Similarity	NPD4600	Approved
0.707	Intermediate Similarity	NPD6995	Phase 1
0.7048	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5901	Discontinued
0.7016	Intermediate Similarity	NPD750	Phase 2
0.7	Intermediate Similarity	NPD1325	Approved
0.7	Intermediate Similarity	NPD1326	Approved
0.6989	Remote Similarity	NPD1630	Approved
0.6967	Remote Similarity	NPD8096	Phase 3
0.6967	Remote Similarity	NPD8097	Phase 3
0.6959	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5426	Phase 3
0.695	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4501	Approved
0.6927	Remote Similarity	NPD4500	Approved
0.6923	Remote Similarity	NPD7001	Phase 3
0.6923	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7946	Pre-registration
0.6875	Remote Similarity	NPD8283	Approved
0.6875	Remote Similarity	NPD8282	Approved
0.6875	Remote Similarity	NPD56	Approved
0.6872	Remote Similarity	NPD1587	Approved
0.6864	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD8399	Phase 1
0.6857	Remote Similarity	NPD8423	Phase 2
0.6853	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6770	Approved
0.6847	Remote Similarity	NPD6962	Phase 2
0.6845	Remote Similarity	NPD484	Approved
0.6845	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6595	Phase 3
0.6837	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5473	Discontinued
0.6827	Remote Similarity	NPD2920	Discontinued
0.6823	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD3947	Discontinued
0.6794	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD8098	Approved
0.6789	Remote Similarity	NPD5138	Approved
0.6789	Remote Similarity	NPD5140	Approved
0.6786	Remote Similarity	NPD4373	Phase 2
0.6768	Remote Similarity	NPD5596	Phase 2
0.6765	Remote Similarity	NPD4602	Approved
0.6762	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD1643	Phase 3
0.6748	Remote Similarity	NPD53	Approved
0.6748	Remote Similarity	NPD7777	Approved
0.6748	Remote Similarity	NPD7778	Approved
0.6743	Remote Similarity	NPD6242	Discontinued
0.6735	Remote Similarity	NPD7865	Approved
0.6734	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD5632	Approved
0.6726	Remote Similarity	NPD4952	Phase 3
0.672	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD1586	Approved
0.6717	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD6999	Discontinued
0.6714	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD8386	Phase 2
0.6683	Remote Similarity	NPD3319	Phase 1
0.6683	Remote Similarity	NPD3318	Approved
0.6683	Remote Similarity	NPD3320	Approved
0.6682	Remote Similarity	NPD7470	Discontinued
0.6682	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5898	Approved
0.6667	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5897	Approved
0.6667	Remote Similarity	NPD5899	Approved
0.6667	Remote Similarity	NPD5293	Phase 2
0.6651	Remote Similarity	NPD7454	Approved
0.6651	Remote Similarity	NPD7455	Approved
0.6637	Remote Similarity	NPD4845	Discontinued
0.6636	Remote Similarity	NPD6733	Discontinued
0.6636	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD8115	Approved
0.6635	Remote Similarity	NPD8114	Approved
0.6633	Remote Similarity	NPD3178	Discontinued
0.6632	Remote Similarity	NPD2214	Approved
0.6632	Remote Similarity	NPD2213	Approved
0.662	Remote Similarity	NPD3794	Approved
0.662	Remote Similarity	NPD3795	Approved
0.6619	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD2336	Approved
0.6614	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD5416	Discontinued
0.6605	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD7944	Discontinued
0.6599	Remote Similarity	NPD5471	Phase 3
0.6588	Remote Similarity	NPD8072	Approved
0.6578	Remote Similarity	NPD4463	Approved
0.6578	Remote Similarity	NPD4462	Approved
0.6573	Remote Similarity	NPD8322	Phase 2
0.6571	Remote Similarity	NPD7727	Phase 2
0.6571	Remote Similarity	NPD7817	Phase 1
0.6566	Remote Similarity	NPD2144	Approved
0.6557	Remote Similarity	NPD8272	Phase 2
0.6555	Remote Similarity	NPD1768	Approved
0.6553	Remote Similarity	NPD1038	Approved
0.6552	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7688	Phase 1
0.654	Remote Similarity	NPD8073	Approved
0.6537	Remote Similarity	NPD5913	Phase 3
0.6537	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD4076	Approved
0.6533	Remote Similarity	NPD4079	Approved
0.6526	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD2008	Discontinued
0.6526	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7957	Phase 1
0.6526	Remote Similarity	NPD3003	Approved
0.6515	Remote Similarity	NPD2382	Approved
0.6515	Remote Similarity	NPD2380	Approved
0.6515	Remote Similarity	NPD3004	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD2381	Approved
0.6514	Remote Similarity	NPD7707	Approved
0.6513	Remote Similarity	NPD7866	Approved
0.6507	Remote Similarity	NPD3006	Discontinued
0.6507	Remote Similarity	NPD4397	Phase 1
0.6504	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD43	Approved
0.6497	Remote Similarity	NPD6182	Approved
0.6497	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.649	Remote Similarity	NPD2307	Discontinued
0.6489	Remote Similarity	NPD3259	Approved
0.6489	Remote Similarity	NPD6164	Phase 2
0.6489	Remote Similarity	NPD6165	Phase 2
0.6482	Remote Similarity	NPD3506	Approved
0.6482	Remote Similarity	NPD7869	Discontinued
0.6482	Remote Similarity	NPD3505	Approved
0.6482	Remote Similarity	NPD6642	Approved
0.6482	Remote Similarity	NPD6641	Approved
0.6481	Remote Similarity	NPD4051	Discontinued
0.6481	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD802	Phase 2
0.6471	Remote Similarity	NPD3258	Approved
0.6468	Remote Similarity	NPD3038	Discontinued
0.6465	Remote Similarity	NPD7665	Phase 2
0.6465	Remote Similarity	NPD7666	Phase 3
0.6465	Remote Similarity	NPD5065	Approved
0.6465	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6376	Discontinued
0.6465	Remote Similarity	NPD2916	Discontinued
0.6453	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5475	Discontinued
0.6449	Remote Similarity	NPD7568	Phase 1
0.6448	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5472	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD3960	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