NPASS Compound

Structure

NPC106833 OpenBabel07101719152D 32 34 0 0 0 0 0 0 0 0999 V2000 12.2094 -4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3434 -4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3434 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4773 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4773 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6113 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6113 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 -1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 24 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 2 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 20 1 0 0 0 0 18 19 2 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 20 25 1 0 0 0 0 21 26 2 0 0 0 0 22 28 2 0 0 0 0 23 27 1 0 0 0 0 23 29 2 0 0 0 0 24 25 2 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 26 27 1 0 0 0 0 26 28 1 0 0 0 0 27 30 2 0 0 0 0 28 31 1 0 0 0 0 29 32 1 0 0 0 0 30 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	659.33
Volume:	648.528
LogP:	1.811
LogD:	1.711
LogS:	-3.96
# Rotatable Bonds:	12
TPSA:	142.45
# H-Bond Aceptor:	12
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.353
Synthetic Accessibility Score:	7.194
Fsp3:	0.771
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.349
MDCK Permeability:	8.749461267143488e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.177
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.219

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.067
Plasma Protein Binding (PPB):	23.239755630493164%
Volume Distribution (VD):	0.765
Pgp-substrate:	49.64419174194336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.827
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.757
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.098
CYP2D6-substrate:	0.568
CYP3A4-inhibitor:	0.805
CYP3A4-substrate:	0.58

ADMET: Excretion

Clearance (CL):	5.678
Half-life (T1/2):	0.416

ADMET: Toxicity

hERG Blockers:	0.921
Human Hepatotoxicity (H-HT):	0.933
Drug-inuced Liver Injury (DILI):	0.221
AMES Toxicity:	0.064
Rat Oral Acute Toxicity:	0.69
Maximum Recommended Daily Dose:	0.76
Skin Sensitization:	0.165
Carcinogencity:	0.018
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC106833

Natural Product ID:	NPC106833
*Common Name:**	Lipocarbazole A3
IUPAC Name:	1-[(Z)-heptadec-8-enyl]-2-methyl-9H-carbazol-3-ol
Synonyms:	Lipocarbazole A3
Standard InCHIKey:	PLBRTTUILORDMU-KHPPLWFESA-N
Standard InCHI:	InChI=1S/C30H43NO/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20-25-24(2)29(32)23-27-26-21-18-19-22-28(26)31-30(25)27/h10-11,18-19,21-23,31-32H,3-9,12-17,20H2,1-2H3/b11-10-
SMILES:	CCCCCCCC/C=CCCCCCCCc1c(C)c(cc2c3ccccc3[nH]c12)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1080115
PubChem CID:	44514059
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
NPO32580	tsukamurella pseudospumae acta 1857	Species	Tsukamurellaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19848432]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	8700.0	nM	PMID[533266]

☑ 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 NPC106833 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	568
0.1-0.2	3068
0.2-0.3	13740
0.3-0.4	8986
0.4-0.5	11054
0.5-0.6	3217
0.6-0.7	1622
0.7-0.8	384
0.8-0.85	40
0.85-0.9	10
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469497
0.994	High Similarity	NPC128751
0.9706	High Similarity	NPC246700
0.9322	High Similarity	NPC153042
0.9235	High Similarity	NPC88363
0.8871	High Similarity	NPC193777
0.8864	High Similarity	NPC94943
0.8807	High Similarity	NPC190007
0.8779	High Similarity	NPC474409
0.875	High Similarity	NPC212535
0.8684	High Similarity	NPC9894
0.8639	High Similarity	NPC48353
0.847	Intermediate Similarity	NPC99666
0.8398	Intermediate Similarity	NPC171171
0.8389	Intermediate Similarity	NPC204717
0.8387	Intermediate Similarity	NPC70956
0.8387	Intermediate Similarity	NPC243834
0.8343	Intermediate Similarity	NPC314002
0.8333	Intermediate Similarity	NPC220765
0.829	Intermediate Similarity	NPC201697
0.828	Intermediate Similarity	NPC131017
0.8274	Intermediate Similarity	NPC314552
0.8268	Intermediate Similarity	NPC72980
0.822	Intermediate Similarity	NPC223427
0.8212	Intermediate Similarity	NPC184964
0.8205	Intermediate Similarity	NPC208284
0.8191	Intermediate Similarity	NPC77555
0.8177	Intermediate Similarity	NPC475070
0.8168	Intermediate Similarity	NPC475112
0.8168	Intermediate Similarity	NPC291535
0.8168	Intermediate Similarity	NPC475085
0.8158	Intermediate Similarity	NPC249040
0.8142	Intermediate Similarity	NPC476319
0.8132	Intermediate Similarity	NPC176127
0.8125	Intermediate Similarity	NPC162484
0.8122	Intermediate Similarity	NPC478074
0.8103	Intermediate Similarity	NPC476116
0.8098	Intermediate Similarity	NPC209174
0.8085	Intermediate Similarity	NPC276517
0.8073	Intermediate Similarity	NPC135887
0.8073	Intermediate Similarity	NPC199277
0.8071	Intermediate Similarity	NPC294620
0.8058	Intermediate Similarity	NPC477531
0.805	Intermediate Similarity	NPC477609
0.8049	Intermediate Similarity	NPC252251
0.801	Intermediate Similarity	NPC128823
0.8	Intermediate Similarity	NPC470126
0.798	Intermediate Similarity	NPC473180
0.7961	Intermediate Similarity	NPC253580
0.7947	Intermediate Similarity	NPC70259
0.7927	Intermediate Similarity	NPC267423
0.7914	Intermediate Similarity	NPC242928
0.791	Intermediate Similarity	NPC293151
0.7906	Intermediate Similarity	NPC156704
0.7906	Intermediate Similarity	NPC474188
0.7895	Intermediate Similarity	NPC205934
0.7895	Intermediate Similarity	NPC195314
0.7895	Intermediate Similarity	NPC43787
0.7882	Intermediate Similarity	NPC86078
0.7879	Intermediate Similarity	NPC5145
0.7865	Intermediate Similarity	NPC72211
0.7861	Intermediate Similarity	NPC46580
0.7857	Intermediate Similarity	NPC476106
0.7853	Intermediate Similarity	NPC251090
0.7853	Intermediate Similarity	NPC205403
0.7846	Intermediate Similarity	NPC476098
0.7843	Intermediate Similarity	NPC280799
0.7842	Intermediate Similarity	NPC307963
0.7839	Intermediate Similarity	NPC23294
0.7839	Intermediate Similarity	NPC294375
0.7833	Intermediate Similarity	NPC280548
0.7809	Intermediate Similarity	NPC159319
0.7805	Intermediate Similarity	NPC280272
0.7789	Intermediate Similarity	NPC303951
0.7788	Intermediate Similarity	NPC477607
0.7788	Intermediate Similarity	NPC477608
0.7784	Intermediate Similarity	NPC329793
0.7784	Intermediate Similarity	NPC213308
0.7784	Intermediate Similarity	NPC474798
0.7778	Intermediate Similarity	NPC76748
0.7778	Intermediate Similarity	NPC202503
0.7772	Intermediate Similarity	NPC183407
0.7772	Intermediate Similarity	NPC469928
0.7767	Intermediate Similarity	NPC51388
0.7761	Intermediate Similarity	NPC266931
0.7761	Intermediate Similarity	NPC477610
0.776	Intermediate Similarity	NPC242209
0.7755	Intermediate Similarity	NPC477135
0.7753	Intermediate Similarity	NPC315214
0.7753	Intermediate Similarity	NPC47298
0.7747	Intermediate Similarity	NPC259545
0.7745	Intermediate Similarity	NPC473179
0.7742	Intermediate Similarity	NPC19679
0.7739	Intermediate Similarity	NPC473181
0.7739	Intermediate Similarity	NPC209769
0.7737	Intermediate Similarity	NPC92111
0.7734	Intermediate Similarity	NPC476041
0.7734	Intermediate Similarity	NPC304926
0.7727	Intermediate Similarity	NPC141353
0.7725	Intermediate Similarity	NPC296527
0.7725	Intermediate Similarity	NPC32771
0.7709	Intermediate Similarity	NPC32028
0.7708	Intermediate Similarity	NPC326634
0.77	Intermediate Similarity	NPC6786
0.77	Intermediate Similarity	NPC199667
0.7696	Intermediate Similarity	NPC114335
0.7696	Intermediate Similarity	NPC280964
0.7696	Intermediate Similarity	NPC141915
0.7692	Intermediate Similarity	NPC227908
0.7692	Intermediate Similarity	NPC315491
0.7692	Intermediate Similarity	NPC45459
0.7688	Intermediate Similarity	NPC210828
0.7688	Intermediate Similarity	NPC86834
0.768	Intermediate Similarity	NPC154293
0.7677	Intermediate Similarity	NPC300156
0.7677	Intermediate Similarity	NPC45190
0.767	Intermediate Similarity	NPC477532
0.7653	Intermediate Similarity	NPC476044
0.765	Intermediate Similarity	NPC313791
0.765	Intermediate Similarity	NPC471294
0.7642	Intermediate Similarity	NPC473182
0.7641	Intermediate Similarity	NPC32200
0.7641	Intermediate Similarity	NPC476175
0.7641	Intermediate Similarity	NPC476167
0.7638	Intermediate Similarity	NPC270918
0.7638	Intermediate Similarity	NPC283117
0.7634	Intermediate Similarity	NPC198339
0.7634	Intermediate Similarity	NPC478032
0.7627	Intermediate Similarity	NPC184476
0.7622	Intermediate Similarity	NPC96890
0.7612	Intermediate Similarity	NPC11464
0.7606	Intermediate Similarity	NPC84478
0.7604	Intermediate Similarity	NPC324149
0.7602	Intermediate Similarity	NPC176538
0.7602	Intermediate Similarity	NPC60553
0.76	Intermediate Similarity	NPC470931
0.76	Intermediate Similarity	NPC39679
0.759	Intermediate Similarity	NPC192315
0.759	Intermediate Similarity	NPC306376
0.7581	Intermediate Similarity	NPC232340
0.7581	Intermediate Similarity	NPC472443
0.7577	Intermediate Similarity	NPC222018
0.7577	Intermediate Similarity	NPC472193
0.7571	Intermediate Similarity	NPC473185
0.7565	Intermediate Similarity	NPC106937
0.7556	Intermediate Similarity	NPC16667
0.7554	Intermediate Similarity	NPC97525
0.7554	Intermediate Similarity	NPC34508
0.7553	Intermediate Similarity	NPC472444
0.755	Intermediate Similarity	NPC88008
0.7549	Intermediate Similarity	NPC118228
0.7541	Intermediate Similarity	NPC126481
0.7536	Intermediate Similarity	NPC132642
0.7536	Intermediate Similarity	NPC150239
0.7528	Intermediate Similarity	NPC285469
0.7525	Intermediate Similarity	NPC471304
0.7514	Intermediate Similarity	NPC472587
0.7512	Intermediate Similarity	NPC211416
0.7512	Intermediate Similarity	NPC477111
0.7512	Intermediate Similarity	NPC3207
0.75	Intermediate Similarity	NPC11408
0.75	Intermediate Similarity	NPC95783
0.75	Intermediate Similarity	NPC314394
0.75	Intermediate Similarity	NPC304183
0.7488	Intermediate Similarity	NPC6215
0.7486	Intermediate Similarity	NPC44161
0.7485	Intermediate Similarity	NPC312092
0.7474	Intermediate Similarity	NPC475190
0.7472	Intermediate Similarity	NPC207726
0.7465	Intermediate Similarity	NPC474701
0.7453	Intermediate Similarity	NPC274640
0.7451	Intermediate Similarity	NPC316981
0.7451	Intermediate Similarity	NPC94157
0.745	Intermediate Similarity	NPC470930
0.7444	Intermediate Similarity	NPC67056
0.7441	Intermediate Similarity	NPC214980
0.744	Intermediate Similarity	NPC247803
0.744	Intermediate Similarity	NPC46561
0.7431	Intermediate Similarity	NPC217554
0.743	Intermediate Similarity	NPC132329
0.7427	Intermediate Similarity	NPC74969
0.7424	Intermediate Similarity	NPC329747
0.7419	Intermediate Similarity	NPC472586
0.7413	Intermediate Similarity	NPC477113
0.7411	Intermediate Similarity	NPC473747
0.7409	Intermediate Similarity	NPC160898
0.7407	Intermediate Similarity	NPC295228
0.7403	Intermediate Similarity	NPC131718
0.7402	Intermediate Similarity	NPC87413
0.7394	Intermediate Similarity	NPC270009
0.7382	Intermediate Similarity	NPC473189
0.7381	Intermediate Similarity	NPC475450
0.7381	Intermediate Similarity	NPC144452
0.7381	Intermediate Similarity	NPC162748
0.7379	Intermediate Similarity	NPC470549
0.7376	Intermediate Similarity	NPC321428
0.7368	Intermediate Similarity	NPC225279
0.7368	Intermediate Similarity	NPC276657
0.7366	Intermediate Similarity	NPC219087
0.7356	Intermediate Similarity	NPC184408

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 NPC106833 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	347
0.1-0.2	686
0.2-0.3	845
0.3-0.4	1442
0.4-0.5	2985
0.5-0.6	2106
0.6-0.7	641
0.7-0.8	93
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8424	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.8307	Intermediate Similarity	NPD4511	Phase 1
0.8274	Intermediate Similarity	NPD5164	Discontinued
0.8136	Intermediate Similarity	NPD1325	Approved
0.8136	Intermediate Similarity	NPD1326	Approved
0.7929	Intermediate Similarity	NPD5939	Approved
0.7929	Intermediate Similarity	NPD5936	Approved
0.7917	Intermediate Similarity	NPD8395	Approved
0.7917	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD8396	Approved
0.7906	Intermediate Similarity	NPD7948	Phase 1
0.7842	Intermediate Similarity	NPD1038	Approved
0.7838	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD1685	Approved
0.7753	Intermediate Similarity	NPD1684	Approved
0.7749	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD2175	Phase 3
0.7732	Intermediate Similarity	NPD2176	Approved
0.7732	Intermediate Similarity	NPD2177	Approved
0.7704	Intermediate Similarity	NPD6975	Discontinued
0.7692	Intermediate Similarity	NPD484	Approved
0.7688	Intermediate Similarity	NPD2916	Discontinued
0.7642	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5658	Approved
0.7598	Intermediate Similarity	NPD5612	Discontinued
0.7598	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD3003	Approved
0.7565	Intermediate Similarity	NPD802	Phase 2
0.7551	Intermediate Similarity	NPD3814	Phase 1
0.755	Intermediate Similarity	NPD7452	Approved
0.755	Intermediate Similarity	NPD7453	Approved
0.755	Intermediate Similarity	NPD7222	Phase 2
0.7514	Intermediate Similarity	NPD5254	Discontinued
0.75	Intermediate Similarity	NPD1592	Phase 3
0.75	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4462	Approved
0.75	Intermediate Similarity	NPD4463	Approved
0.7487	Intermediate Similarity	NPD2383	Phase 1
0.7463	Intermediate Similarity	NPD6290	Phase 2
0.745	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4418	Discontinued
0.7433	Intermediate Similarity	NPD6159	Phase 2
0.743	Intermediate Similarity	NPD2789	Approved
0.7419	Intermediate Similarity	NPD5065	Approved
0.7413	Intermediate Similarity	NPD5530	Phase 1
0.7403	Intermediate Similarity	NPD5599	Discontinued
0.7402	Intermediate Similarity	NPD4502	Phase 2
0.7396	Intermediate Similarity	NPD8431	Approved
0.7377	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5913	Phase 3
0.7371	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6158	Phase 2
0.736	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD2021	Discontinued
0.735	Intermediate Similarity	NPD3928	Approved
0.735	Intermediate Similarity	NPD3931	Approved
0.7343	Intermediate Similarity	NPD7112	Discontinued
0.7323	Intermediate Similarity	NPD2727	Phase 2
0.7302	Intermediate Similarity	NPD3920	Phase 2
0.7299	Intermediate Similarity	NPD7219	Approved
0.7299	Intermediate Similarity	NPD7221	Approved
0.7297	Intermediate Similarity	NPD2844	Phase 3
0.7295	Intermediate Similarity	NPD5902	Approved
0.7295	Intermediate Similarity	NPD5903	Approved
0.7292	Intermediate Similarity	NPD2762	Phase 2
0.7286	Intermediate Similarity	NPD3825	Phase 3
0.7286	Intermediate Similarity	NPD1768	Approved
0.7282	Intermediate Similarity	NPD2794	Discontinued
0.7277	Intermediate Similarity	NPD4795	Phase 2
0.7273	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5003	Discontinued
0.7269	Intermediate Similarity	NPD3746	Discontinued
0.7263	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD2882	Phase 1
0.7259	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6376	Discontinued
0.7255	Intermediate Similarity	NPD2187	Approved
0.7255	Intermediate Similarity	NPD2189	Approved
0.724	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD2920	Discontinued
0.7228	Intermediate Similarity	NPD5138	Approved
0.7228	Intermediate Similarity	NPD5140	Approved
0.7216	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD8386	Phase 2
0.7204	Intermediate Similarity	NPD1921	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2564	Approved
0.7143	Intermediate Similarity	NPD2565	Phase 2
0.7143	Intermediate Similarity	NPD7324	Discontinued
0.7136	Intermediate Similarity	NPD3127	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6242	Discontinued
0.712	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD8358	Approved
0.7105	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5100	Phase 3
0.7105	Intermediate Similarity	NPD2380	Approved
0.7105	Intermediate Similarity	NPD2382	Approved
0.7105	Intermediate Similarity	NPD2381	Approved
0.7092	Intermediate Similarity	NPD1534	Approved
0.709	Intermediate Similarity	NPD7418	Discontinued
0.7089	Intermediate Similarity	NPD7726	Phase 1
0.7089	Intermediate Similarity	NPD5506	Approved
0.7089	Intermediate Similarity	NPD5507	Approved
0.7081	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD1740	Approved
0.7079	Intermediate Similarity	NPD1739	Approved
0.7074	Intermediate Similarity	NPD7474	Suspended
0.7073	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD1262	Discovery
0.7068	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5067	Phase 2
0.7067	Intermediate Similarity	NPD5066	Phase 2
0.7053	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7555	Discontinued
0.705	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4203	Approved
0.7047	Intermediate Similarity	NPD4204	Approved
0.7045	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6145	Phase 1
0.7042	Intermediate Similarity	NPD5930	Phase 3
0.7039	Intermediate Similarity	NPD1392	Approved
0.7039	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5429	Discontinued
0.7037	Intermediate Similarity	NPD7603	Discontinued
0.7037	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD8093	Discontinued
0.7033	Intermediate Similarity	NPD3330	Phase 1
0.7032	Intermediate Similarity	NPD5151	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD6985	Discontinued
0.7026	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5901	Discontinued
0.7	Intermediate Similarity	NPD2615	Phase 3
0.7	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8094	Discontinued
0.7	Intermediate Similarity	NPD7558	Phase 2
0.7	Intermediate Similarity	NPD2616	Phase 3
0.6995	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7194	Discontinued
0.6995	Remote Similarity	NPD6595	Phase 3
0.6991	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6220	Phase 3
0.6985	Remote Similarity	NPD3404	Approved
0.6984	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD4044	Discontinued
0.6973	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD6492	Phase 2
0.6943	Remote Similarity	NPD4076	Approved
0.6943	Remote Similarity	NPD4079	Approved
0.6941	Remote Similarity	NPD7567	Approved
0.6935	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD1219	Approved
0.6931	Remote Similarity	NPD5021	Discontinued
0.6931	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD1218	Approved
0.6927	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6494	Phase 2
0.6923	Remote Similarity	NPD5596	Phase 2
0.6916	Remote Similarity	NPD3258	Approved
0.6916	Remote Similarity	NPD3875	Discontinued
0.6916	Remote Similarity	NPD3763	Approved
0.6915	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD8403	Phase 1
0.69	Remote Similarity	NPD3924	Approved
0.69	Remote Similarity	NPD3923	Approved
0.69	Remote Similarity	NPD3922	Approved
0.69	Remote Similarity	NPD3921	Approved
0.6891	Remote Similarity	NPD3505	Approved
0.6891	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD3506	Approved
0.6878	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD9690	Approved
0.6872	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD3525	Discontinued
0.6869	Remote Similarity	NPD5632	Approved
0.6869	Remote Similarity	NPD4951	Discontinued
0.6869	Remote Similarity	NPD3354	Phase 2
0.6869	Remote Similarity	NPD4948	Discontinued
0.6849	Remote Similarity	NPD6978	Phase 2
0.6849	Remote Similarity	NPD4845	Discontinued
0.6849	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD2952	Discontinued
0.6845	Remote Similarity	NPD112	Approved
0.6845	Remote Similarity	NPD9705	Discontinued
0.6844	Remote Similarity	NPD8016	Phase 3
0.6844	Remote Similarity	NPD4561	Discontinued
0.6844	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7671	Approved
0.6842	Remote Similarity	NPD7672	Approved
0.6842	Remote Similarity	NPD5488	Discontinued
0.6834	Remote Similarity	NPD6965	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