NPASS Compound

Structure

CID85651 OpenBabel06191715422D 23 27 0 0 1 0 0 0 0 0999 V2000 -2.4884 1.4933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8350 1.8706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8777 2.9066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4655 2.0975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8832 2.8020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0588 1.1840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9241 1.6001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4256 1.8885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9240 0.5334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0134 1.0795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9236 1.6003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3773 0.6533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3774 1.4802 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0002 2.1337 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4765 1.8885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0642 1.0795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9237 0.5336 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4746 1.5795 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4746 0.5795 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4765 0.2705 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.4746 2.5795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4256 0.2705 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 15 2 0 0 0 0 6 16 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 21 1 0 0 0 0 10 23 1 0 0 0 0 11 14 1 0 0 0 0 11 17 1 0 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 2 1 6 0 0 0 13 14 1 0 0 0 0 14 7 1 1 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 17 21 1 1 0 0 0 18 19 1 6 0 0 0 18 22 1 0 0 0 0 19 20 1 1 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.18
Volume:	323.426
LogP:	2.968
LogD:	3.006
LogS:	-3.945
# Rotatable Bonds:	2
TPSA:	44.73
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.823
Synthetic Accessibility Score:	5.381
Fsp3:	0.579
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:	-4.887
MDCK Permeability:	2.1770729290437885e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.936
Human Intestinal Absorption (HIA):	0.071
20% Bioavailability (F20%):	0.185
30% Bioavailability (F30%):	0.504

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.989
Plasma Protein Binding (PPB):	67.88253784179688%
Volume Distribution (VD):	2.411
Pgp-substrate:	36.69270706176758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.068
CYP1A2-substrate:	0.444
CYP2C19-inhibitor:	0.136
CYP2C19-substrate:	0.851
CYP2C9-inhibitor:	0.171
CYP2C9-substrate:	0.104
CYP2D6-inhibitor:	0.136
CYP2D6-substrate:	0.802
CYP3A4-inhibitor:	0.773
CYP3A4-substrate:	0.89

ADMET: Excretion

Clearance (CL):	6.803
Half-life (T1/2):	0.318

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.871
Drug-inuced Liver Injury (DILI):	0.193
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.428
Maximum Recommended Daily Dose:	0.879
Skin Sensitization:	0.158
Carcinogencity:	0.88
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.918

Download Data

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

Natural Product: NPC85651

Natural Product ID:	NPC85651
*Common Name:**	3-Epiquinamine
IUPAC Name:	(3aS,8bR)-3a-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-2,4-dihydro-1H-furo[2,3-b]indol-8b-ol
Synonyms:
Standard InCHIKey:	ALNKTVLUDWIWIH-JCTKKGROSA-N
Standard InCHI:	InChI=1S/C19H24N2O2/c1-2-13-12-21-9-7-14(13)11-17(21)19-18(22,8-10-23-19)15-5-3-4-6-16(15)20-19/h2-6,13-14,17,20,22H,1,7-12H2/t13-,14-,17+,18+,19-/m0/s1
SMILES:	C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@@]12OCC[C@@]2(O)c2c(N1)cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2262629
PubChem CID:	76319464
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001146] Indolines

*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
NPO25089	Cinchona calisaya	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11992775]
NPO765	Holarrhena pubescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO765	Holarrhena pubescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25089	Cinchona calisaya	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO765	Holarrhena pubescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO765	Holarrhena pubescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25089	Cinchona calisaya	Species	Rubiaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	12.9	ug.mL-1	PMID[489812]

☑ 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 NPC85651 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	315
0.1-0.2	1310
0.2-0.3	5478
0.3-0.4	18751
0.4-0.5	11636
0.5-0.6	4348
0.6-0.7	801
0.7-0.8	55
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8012	Intermediate Similarity	NPC472115
0.8012	Intermediate Similarity	NPC472114
0.7784	Intermediate Similarity	NPC313757
0.7614	Intermediate Similarity	NPC477159
0.7531	Intermediate Similarity	NPC472100
0.7531	Intermediate Similarity	NPC264589
0.7529	Intermediate Similarity	NPC129624
0.7407	Intermediate Similarity	NPC472103
0.7399	Intermediate Similarity	NPC472118
0.7349	Intermediate Similarity	NPC475763
0.7312	Intermediate Similarity	NPC90967
0.7294	Intermediate Similarity	NPC471122
0.7289	Intermediate Similarity	NPC318086
0.7253	Intermediate Similarity	NPC181928
0.7232	Intermediate Similarity	NPC476441
0.7225	Intermediate Similarity	NPC472106
0.7222	Intermediate Similarity	NPC256288
0.7209	Intermediate Similarity	NPC472101
0.7209	Intermediate Similarity	NPC176983
0.7209	Intermediate Similarity	NPC472120
0.7182	Intermediate Similarity	NPC2933
0.7174	Intermediate Similarity	NPC473298
0.7151	Intermediate Similarity	NPC472102
0.7151	Intermediate Similarity	NPC309531
0.7143	Intermediate Similarity	NPC259626
0.7143	Intermediate Similarity	NPC476095
0.7143	Intermediate Similarity	NPC317430
0.7135	Intermediate Similarity	NPC469428
0.7135	Intermediate Similarity	NPC113946
0.7127	Intermediate Similarity	NPC139291
0.7127	Intermediate Similarity	NPC472109
0.7127	Intermediate Similarity	NPC472108
0.7127	Intermediate Similarity	NPC472110
0.7126	Intermediate Similarity	NPC471124
0.7119	Intermediate Similarity	NPC476425
0.711	Intermediate Similarity	NPC286871
0.7107	Intermediate Similarity	NPC469592
0.7107	Intermediate Similarity	NPC471080
0.7104	Intermediate Similarity	NPC473615
0.7093	Intermediate Similarity	NPC36495
0.7076	Intermediate Similarity	NPC29285
0.7065	Intermediate Similarity	NPC229484
0.7065	Intermediate Similarity	NPC285841
0.705	Intermediate Similarity	NPC469594
0.7043	Intermediate Similarity	NPC470483
0.7043	Intermediate Similarity	NPC25401
0.7033	Intermediate Similarity	NPC159963
0.7027	Intermediate Similarity	NPC292675
0.7022	Intermediate Similarity	NPC477185
0.7021	Intermediate Similarity	NPC34717
0.7016	Intermediate Similarity	NPC249040
0.7011	Intermediate Similarity	NPC472121
0.7011	Intermediate Similarity	NPC472117
0.7	Intermediate Similarity	NPC477187
0.6978	Remote Similarity	NPC314394
0.6968	Remote Similarity	NPC470485
0.6961	Remote Similarity	NPC475094
0.6961	Remote Similarity	NPC218594
0.6961	Remote Similarity	NPC133261
0.6961	Remote Similarity	NPC99043
0.6959	Remote Similarity	NPC478076
0.6954	Remote Similarity	NPC474058
0.6949	Remote Similarity	NPC33507
0.6948	Remote Similarity	NPC475915
0.6944	Remote Similarity	NPC472122
0.6944	Remote Similarity	NPC24594
0.6935	Remote Similarity	NPC284706
0.6927	Remote Similarity	NPC472123
0.6904	Remote Similarity	NPC469589
0.6904	Remote Similarity	NPC477160
0.6898	Remote Similarity	NPC22689
0.6898	Remote Similarity	NPC105055
0.6897	Remote Similarity	NPC193410
0.6893	Remote Similarity	NPC279527
0.6893	Remote Similarity	NPC214960
0.6887	Remote Similarity	NPC101139
0.6885	Remote Similarity	NPC476428
0.6882	Remote Similarity	NPC14994
0.6868	Remote Similarity	NPC321211
0.6857	Remote Similarity	NPC68650
0.6857	Remote Similarity	NPC248117
0.6856	Remote Similarity	NPC471436
0.6851	Remote Similarity	NPC264482
0.6851	Remote Similarity	NPC203202
0.6845	Remote Similarity	NPC477186
0.6839	Remote Similarity	NPC61013
0.6839	Remote Similarity	NPC211525
0.6839	Remote Similarity	NPC153694
0.6836	Remote Similarity	NPC70172
0.6833	Remote Similarity	NPC251212
0.6833	Remote Similarity	NPC285622
0.6833	Remote Similarity	NPC139085
0.6833	Remote Similarity	NPC214626
0.6833	Remote Similarity	NPC473880
0.6831	Remote Similarity	NPC187827
0.6831	Remote Similarity	NPC472105
0.6818	Remote Similarity	NPC99632
0.6818	Remote Similarity	NPC282339
0.6813	Remote Similarity	NPC326575
0.6813	Remote Similarity	NPC211997
0.6813	Remote Similarity	NPC476326
0.6809	Remote Similarity	NPC5630
0.6796	Remote Similarity	NPC475097
0.6786	Remote Similarity	NPC311330
0.6779	Remote Similarity	NPC476492
0.6778	Remote Similarity	NPC158129
0.6774	Remote Similarity	NPC52262
0.6774	Remote Similarity	NPC62510
0.6772	Remote Similarity	NPC203628
0.6763	Remote Similarity	NPC98371
0.6763	Remote Similarity	NPC313884
0.676	Remote Similarity	NPC224970
0.676	Remote Similarity	NPC167724
0.676	Remote Similarity	NPC223595
0.676	Remote Similarity	NPC469462
0.6758	Remote Similarity	NPC320147
0.6758	Remote Similarity	NPC134586
0.6757	Remote Similarity	NPC472444
0.675	Remote Similarity	NPC197680
0.675	Remote Similarity	NPC259098
0.6747	Remote Similarity	NPC243162
0.6746	Remote Similarity	NPC470824
0.6742	Remote Similarity	NPC475420
0.674	Remote Similarity	NPC177261
0.6728	Remote Similarity	NPC476687
0.6728	Remote Similarity	NPC476689
0.6728	Remote Similarity	NPC476685
0.6723	Remote Similarity	NPC476231
0.6721	Remote Similarity	NPC186669
0.672	Remote Similarity	NPC469501
0.672	Remote Similarity	NPC474059
0.672	Remote Similarity	NPC469470
0.672	Remote Similarity	NPC97584
0.672	Remote Similarity	NPC245741
0.6717	Remote Similarity	NPC478075
0.6707	Remote Similarity	NPC22082
0.6707	Remote Similarity	NPC186284
0.6705	Remote Similarity	NPC243673
0.6705	Remote Similarity	NPC63210
0.6705	Remote Similarity	NPC310403
0.6705	Remote Similarity	NPC263709
0.6705	Remote Similarity	NPC97380
0.6705	Remote Similarity	NPC148468
0.6704	Remote Similarity	NPC278887
0.6687	Remote Similarity	NPC208757
0.6685	Remote Similarity	NPC472443
0.6685	Remote Similarity	NPC6974
0.6685	Remote Similarity	NPC476118
0.6684	Remote Similarity	NPC322621
0.6684	Remote Similarity	NPC1464
0.6684	Remote Similarity	NPC133591
0.6683	Remote Similarity	NPC471663
0.6667	Remote Similarity	NPC221687
0.6667	Remote Similarity	NPC230313
0.6667	Remote Similarity	NPC203754
0.6667	Remote Similarity	NPC217294
0.6667	Remote Similarity	NPC150048
0.6667	Remote Similarity	NPC472111
0.6649	Remote Similarity	NPC38823
0.6649	Remote Similarity	NPC291759
0.6649	Remote Similarity	NPC282092
0.6649	Remote Similarity	NPC132874
0.6649	Remote Similarity	NPC138615
0.6649	Remote Similarity	NPC207033
0.6649	Remote Similarity	NPC218733
0.6649	Remote Similarity	NPC265642
0.6648	Remote Similarity	NPC123241
0.6648	Remote Similarity	NPC470069
0.6648	Remote Similarity	NPC52059
0.6646	Remote Similarity	NPC184437
0.6633	Remote Similarity	NPC232600
0.6632	Remote Similarity	NPC303214
0.6631	Remote Similarity	NPC472294
0.663	Remote Similarity	NPC469915
0.663	Remote Similarity	NPC260075
0.6629	Remote Similarity	NPC293458
0.6618	Remote Similarity	NPC234772
0.6618	Remote Similarity	NPC471506
0.6616	Remote Similarity	NPC470484
0.6615	Remote Similarity	NPC32200
0.6614	Remote Similarity	NPC21425
0.6613	Remote Similarity	NPC475962
0.6612	Remote Similarity	NPC470548
0.6603	Remote Similarity	NPC231924
0.6598	Remote Similarity	NPC161804
0.6596	Remote Similarity	NPC473007
0.6591	Remote Similarity	NPC477157
0.6591	Remote Similarity	NPC477156
0.6583	Remote Similarity	NPC475841
0.6583	Remote Similarity	NPC195787
0.6583	Remote Similarity	NPC474145
0.6583	Remote Similarity	NPC246140
0.6582	Remote Similarity	NPC127178
0.658	Remote Similarity	NPC243626
0.6579	Remote Similarity	NPC46413
0.6579	Remote Similarity	NPC175474
0.6578	Remote Similarity	NPC19679
0.6578	Remote Similarity	NPC472104
0.6578	Remote Similarity	NPC98197
0.6574	Remote Similarity	NPC470785

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 NPC85651 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	520
0.2-0.3	598
0.3-0.4	1478
0.4-0.5	3229
0.5-0.6	2808
0.6-0.7	338
0.7-0.8	6
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
0.7683	Intermediate Similarity	NPD4121	Phase 3
0.7683	Intermediate Similarity	NPD4120	Approved
0.7636	Intermediate Similarity	NPD5743	Approved
0.7636	Intermediate Similarity	NPD5741	Approved
0.7636	Intermediate Similarity	NPD5742	Approved
0.7572	Intermediate Similarity	NPD6316	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1405	Approved
0.7097	Intermediate Similarity	NPD6320	Approved
0.7041	Intermediate Similarity	NPD3329	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD1769	Discontinued
0.7033	Intermediate Similarity	NPD5596	Phase 2
0.7017	Intermediate Similarity	NPD6879	Phase 2
0.7017	Intermediate Similarity	NPD6878	Phase 2
0.6988	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6301	Phase 2
0.6885	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4951	Discontinued
0.6851	Remote Similarity	NPD2380	Approved
0.6851	Remote Similarity	NPD2381	Approved
0.6851	Remote Similarity	NPD2382	Approved
0.6845	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6069	Approved
0.6842	Remote Similarity	NPD6070	Approved
0.6832	Remote Similarity	NPD865	Approved
0.6832	Remote Similarity	NPD864	Approved
0.6829	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.679	Remote Similarity	NPD1594	Phase 3
0.679	Remote Similarity	NPD1595	Approved
0.6784	Remote Similarity	NPD6221	Approved
0.6784	Remote Similarity	NPD6222	Approved
0.6774	Remote Similarity	NPD6557	Phase 2
0.677	Remote Similarity	NPD4275	Approved
0.677	Remote Similarity	NPD4274	Approved
0.677	Remote Similarity	NPD3720	Discontinued
0.6763	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.675	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.674	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD4644	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD5582	Discontinued
0.6705	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5938	Phase 3
0.6699	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6978	Phase 2
0.6685	Remote Similarity	NPD5138	Approved
0.6685	Remote Similarity	NPD3824	Phase 1
0.6685	Remote Similarity	NPD7479	Phase 2
0.6685	Remote Similarity	NPD5140	Approved
0.6684	Remote Similarity	NPD6227	Discontinued
0.6667	Remote Similarity	NPD1908	Phase 2
0.665	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6339	Approved
0.6649	Remote Similarity	NPD6340	Approved
0.6649	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD5941	Approved
0.6628	Remote Similarity	NPD5942	Approved
0.6617	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD1294	Discontinued
0.6615	Remote Similarity	NPD7262	Phase 1
0.6608	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6455	Phase 3
0.6598	Remote Similarity	NPD5003	Discontinued
0.6597	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD5913	Phase 3
0.6588	Remote Similarity	NPD2387	Approved
0.6584	Remote Similarity	NPD7247	Discontinued
0.6583	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7890	Discontinued
0.6573	Remote Similarity	NPD6524	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD789	Phase 2
0.6566	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD5723	Approved
0.6556	Remote Similarity	NPD4253	Approved
0.6556	Remote Similarity	NPD4254	Approved
0.6552	Remote Similarity	NPD2398	Phase 3
0.6545	Remote Similarity	NPD6309	Approved
0.6545	Remote Similarity	NPD7630	Phase 3
0.6545	Remote Similarity	NPD6310	Approved
0.6545	Remote Similarity	NPD7628	Phase 3
0.6545	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6311	Approved
0.6541	Remote Similarity	NPD519	Approved
0.6538	Remote Similarity	NPD5657	Phase 3
0.6531	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD4430	Phase 2
0.6524	Remote Similarity	NPD4619	Approved
0.6524	Remote Similarity	NPD4621	Approved
0.6522	Remote Similarity	NPD5466	Approved
0.6519	Remote Similarity	NPD6037	Discontinued
0.6517	Remote Similarity	NPD5255	Approved
0.6514	Remote Similarity	NPD8402	Approved
0.6514	Remote Similarity	NPD8400	Approved
0.6514	Remote Similarity	NPD8401	Approved
0.6509	Remote Similarity	NPD3625	Discontinued
0.6506	Remote Similarity	NPD2791	Discontinued
0.6503	Remote Similarity	NPD3975	Discontinued
0.6503	Remote Similarity	NPD4365	Phase 2
0.6497	Remote Similarity	NPD1922	Discontinued
0.6497	Remote Similarity	NPD2326	Approved
0.6495	Remote Similarity	NPD4602	Approved
0.6491	Remote Similarity	NPD6676	Phase 2
0.6484	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD3983	Phase 3
0.648	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6357	Discontinued
0.6474	Remote Similarity	NPD5256	Discontinued
0.6474	Remote Similarity	NPD1802	Approved
0.6474	Remote Similarity	NPD1801	Approved
0.6471	Remote Similarity	NPD3330	Phase 1
0.6467	Remote Similarity	NPD5997	Discontinued
0.6467	Remote Similarity	NPD1112	Phase 3
0.6467	Remote Similarity	NPD1111	Phase 3
0.6467	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6238	Discontinued
0.6464	Remote Similarity	NPD4796	Discontinued
0.6464	Remote Similarity	NPD5430	Discontinued
0.6459	Remote Similarity	NPD7726	Phase 1
0.6458	Remote Similarity	NPD2843	Phase 2
0.6458	Remote Similarity	NPD2845	Phase 2
0.6452	Remote Similarity	NPD5600	Discontinued
0.6448	Remote Similarity	NPD1325	Approved
0.6448	Remote Similarity	NPD1326	Approved
0.6446	Remote Similarity	NPD5119	Approved
0.6446	Remote Similarity	NPD5121	Approved
0.6446	Remote Similarity	NPD5120	Approved
0.6444	Remote Similarity	NPD1743	Approved
0.6444	Remote Similarity	NPD19	Approved
0.6444	Remote Similarity	NPD1742	Approved
0.6442	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD7194	Discontinued
0.644	Remote Similarity	NPD2383	Phase 1
0.6438	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD7250	Approved
0.6438	Remote Similarity	NPD7249	Approved
0.6436	Remote Similarity	NPD4204	Approved
0.6436	Remote Similarity	NPD4203	Approved
0.6433	Remote Similarity	NPD5024	Approved
0.6432	Remote Similarity	NPD5065	Approved
0.6429	Remote Similarity	NPD4410	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6767	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4411	Phase 1
0.6425	Remote Similarity	NPD4485	Approved
0.6425	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD6283	Phase 2
0.6424	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD3082	Discontinued
0.642	Remote Similarity	NPD3826	Clinical (unspecified phase)
0.642	Remote Similarity	NPD2882	Phase 1
0.642	Remote Similarity	NPD5663	Discontinued
0.6418	Remote Similarity	NPD3003	Approved
0.6414	Remote Similarity	NPD4601	Approved
0.6414	Remote Similarity	NPD4600	Approved
0.6413	Remote Similarity	NPD2215	Approved
0.6413	Remote Similarity	NPD2216	Approved
0.6413	Remote Similarity	NPD4083	Discontinued
0.6408	Remote Similarity	NPD7073	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD2469	Approved
0.6404	Remote Similarity	NPD2468	Approved
0.6404	Remote Similarity	NPD1663	Discontinued
0.6402	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD2565	Phase 2
0.6373	Remote Similarity	NPD2564	Approved
0.6369	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6249	Phase 2
0.6364	Remote Similarity	NPD6248	Phase 2
0.6364	Remote Similarity	NPD5498	Phase 2
0.6359	Remote Similarity	NPD5150	Phase 2
0.6358	Remote Similarity	NPD5060	Phase 1
0.6358	Remote Similarity	NPD7785	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD5184	Approved
0.6347	Remote Similarity	NPD5185	Approved
0.6347	Remote Similarity	NPD5182	Approved
0.6344	Remote Similarity	NPD6492	Phase 2
0.6343	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD3662	Phase 3
0.6341	Remote Similarity	NPD3661	Approved
0.6341	Remote Similarity	NPD3664	Approved
0.6341	Remote Similarity	NPD3663	Approved
0.6333	Remote Similarity	NPD4514	Approved
0.6331	Remote Similarity	NPD5318	Discontinued
0.6328	Remote Similarity	NPD6158	Phase 2
0.6328	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD4150	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7444	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4717	Approved
0.6316	Remote Similarity	NPD4720	Approved
0.6316	Remote Similarity	NPD6985	Discontinued
0.6316	Remote Similarity	NPD4718	Approved

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