NPASS Compound

Structure

NPC474077 OpenBabel07101718312D 29 33 0 0 1 0 0 0 0 0999 V2000 2.9033 0.2653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6006 1.6796 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 0.2660 -2.5820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1856 -2.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9341 -1.1765 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 0.8806 -1.1442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2650 -2.5371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9393 -0.0007 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7374 -1.9332 0.0000 C 0 0 1 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 1.6878 -0.9685 0.0000 C 0 0 2 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 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2447 -1.5172 0.0000 C 0 0 1 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 2.2512 -0.0168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5868 -0.7642 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 1 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 2.0662 -2.5012 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 1.2270 0.7011 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2306 -0.2185 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5337 -2.4637 0.0000 O 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 1.9362 0.9323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 28 1 0 0 0 0 3 29 1 0 0 0 0 4 5 2 0 0 0 0 4 14 1 0 0 0 0 5 17 1 0 0 0 0 6 7 1 0 0 0 0 6 22 1 0 0 0 0 7 24 1 0 0 0 0 8 15 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 11 24 1 0 0 0 0 12 1 1 6 0 0 0 12 25 1 0 0 0 0 13 8 1 1 0 0 0 14 28 1 0 0 0 0 15 12 1 6 0 0 0 15 18 1 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 21 1 1 0 0 0 18 24 1 0 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 19 23 2 0 0 0 0 20 26 2 0 0 0 0 20 29 1 0 0 0 0 21 20 1 6 0 0 0 22 27 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.2
Volume:	399.048
LogP:	1.448
LogD:	1.503
LogS:	-3.643
# Rotatable Bonds:	4
TPSA:	91.59
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.75
Synthetic Accessibility Score:	5.706
Fsp3:	0.636
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.504
MDCK Permeability:	1.5273513781721704e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.886
Human Intestinal Absorption (HIA):	0.747
20% Bioavailability (F20%):	0.082
30% Bioavailability (F30%):	0.816

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.92
Plasma Protein Binding (PPB):	72.02423858642578%
Volume Distribution (VD):	2.27
Pgp-substrate:	33.26426315307617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.061
CYP1A2-substrate:	0.906
CYP2C19-inhibitor:	0.143
CYP2C19-substrate:	0.899
CYP2C9-inhibitor:	0.071
CYP2C9-substrate:	0.198
CYP2D6-inhibitor:	0.073
CYP2D6-substrate:	0.888
CYP3A4-inhibitor:	0.227
CYP3A4-substrate:	0.821

ADMET: Excretion

Clearance (CL):	5.527
Half-life (T1/2):	0.334

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.902
Drug-inuced Liver Injury (DILI):	0.237
AMES Toxicity:	0.827
Rat Oral Acute Toxicity:	0.881
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.057
Carcinogencity:	0.961
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.928

Download Data

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

Natural Product: NPC474077

Natural Product ID:	NPC474077
*Common Name:**	MMANMJCGIGNJGH-PMELCEAWSA-N
IUPAC Name:	n.a.
Synonyms:	19-Epi-Voacristine Hydroxyindolenine
Standard InCHIKey:	MMANMJCGIGNJGH-PMELCEAWSA-N
Standard InCHI:	InChI=1S/C22H28N2O5/c1-12(25)15-8-13-10-21(20(26)29-3)18(15)24(11-13)7-6-22(27)16-9-14(28-2)4-5-17(16)23-19(21)22/h4-5,9,12-13,15,18,25,27H,6-8,10-11H2,1-3H3/t12-,13+,15-,18+,21+,22-/m1/s1
SMILES:	CC(C1CC2CC3(C1N(C2)CCC4(C3=NC5=C4C=C(C=C5)OC)O)C(=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460120
PubChem CID:	44566748
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002748] Ibogan-type alkaloids

*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
NPO32495	tabernaemontana calcarea	Species	Apocynaceae	Eukaryota	n.a.	Madagascar rainforest	n.a.	PMID[12713407]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	10.8	ug.mL-1	PMID[559501]

☑ 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 NPC474077 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	293
0.1-0.2	1223
0.2-0.3	3421
0.3-0.4	10701
0.4-0.5	11085
0.5-0.6	14143
0.6-0.7	1697
0.7-0.8	126
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9553	High Similarity	NPC203972
0.8994	High Similarity	NPC475962
0.8333	Intermediate Similarity	NPC278887
0.822	Intermediate Similarity	NPC28510
0.7944	Intermediate Similarity	NPC475720
0.7944	Intermediate Similarity	NPC474192
0.7861	Intermediate Similarity	NPC21752
0.7861	Intermediate Similarity	NPC276993
0.7861	Intermediate Similarity	NPC298851
0.7861	Intermediate Similarity	NPC210415
0.7861	Intermediate Similarity	NPC293255
0.7861	Intermediate Similarity	NPC181138
0.7835	Intermediate Similarity	NPC217294
0.7727	Intermediate Similarity	NPC475816
0.7692	Intermediate Similarity	NPC21425
0.7661	Intermediate Similarity	NPC473105
0.7619	Intermediate Similarity	NPC234772
0.7577	Intermediate Similarity	NPC98197
0.7524	Intermediate Similarity	NPC195787
0.7524	Intermediate Similarity	NPC246140
0.7512	Intermediate Similarity	NPC473458
0.75	Intermediate Similarity	NPC168250
0.75	Intermediate Similarity	NPC52059
0.75	Intermediate Similarity	NPC470069
0.7473	Intermediate Similarity	NPC263709
0.7473	Intermediate Similarity	NPC63210
0.7473	Intermediate Similarity	NPC97380
0.7473	Intermediate Similarity	NPC148468
0.7473	Intermediate Similarity	NPC310403
0.7473	Intermediate Similarity	NPC243673
0.745	Intermediate Similarity	NPC204970
0.7419	Intermediate Similarity	NPC153694
0.7419	Intermediate Similarity	NPC211525
0.7397	Intermediate Similarity	NPC311906
0.7391	Intermediate Similarity	NPC87714
0.7391	Intermediate Similarity	NPC14339
0.7383	Intermediate Similarity	NPC96321
0.7366	Intermediate Similarity	NPC138830
0.7312	Intermediate Similarity	NPC161827
0.7295	Intermediate Similarity	NPC1464
0.7286	Intermediate Similarity	NPC291759
0.7285	Intermediate Similarity	NPC477397
0.7281	Intermediate Similarity	NPC128476
0.7273	Intermediate Similarity	NPC471513
0.7269	Intermediate Similarity	NPC288110
0.7269	Intermediate Similarity	NPC108826
0.7251	Intermediate Similarity	NPC477160
0.7243	Intermediate Similarity	NPC189661
0.7238	Intermediate Similarity	NPC478075
0.7236	Intermediate Similarity	NPC469460
0.7236	Intermediate Similarity	NPC133591
0.7236	Intermediate Similarity	NPC473007
0.7235	Intermediate Similarity	NPC10653
0.7235	Intermediate Similarity	NPC318525
0.723	Intermediate Similarity	NPC472098
0.722	Intermediate Similarity	NPC272706
0.7209	Intermediate Similarity	NPC469928
0.72	Intermediate Similarity	NPC38823
0.72	Intermediate Similarity	NPC207033
0.7182	Intermediate Similarity	NPC19175
0.7178	Intermediate Similarity	NPC174629
0.7178	Intermediate Similarity	NPC473008
0.715	Intermediate Similarity	NPC469462
0.7149	Intermediate Similarity	NPC476436
0.7137	Intermediate Similarity	NPC301501
0.7137	Intermediate Similarity	NPC329982
0.7135	Intermediate Similarity	NPC70172
0.712	Intermediate Similarity	NPC472100
0.7097	Intermediate Similarity	NPC195636
0.7094	Intermediate Similarity	NPC5630
0.7091	Intermediate Similarity	NPC71539
0.7091	Intermediate Similarity	NPC250960
0.707	Intermediate Similarity	NPC127996
0.7056	Intermediate Similarity	NPC269449
0.7056	Intermediate Similarity	NPC471304
0.7042	Intermediate Similarity	NPC329329
0.7042	Intermediate Similarity	NPC317709
0.7034	Intermediate Similarity	NPC478080
0.7028	Intermediate Similarity	NPC472111
0.7027	Intermediate Similarity	NPC231924
0.7024	Intermediate Similarity	NPC473004
0.701	Intermediate Similarity	NPC474059
0.7	Intermediate Similarity	NPC477157
0.7	Intermediate Similarity	NPC472099
0.7	Intermediate Similarity	NPC10875
0.7	Intermediate Similarity	NPC10730
0.7	Intermediate Similarity	NPC476069
0.7	Intermediate Similarity	NPC477156
0.6996	Remote Similarity	NPC266994
0.6991	Remote Similarity	NPC139373
0.6991	Remote Similarity	NPC10732
0.6991	Remote Similarity	NPC119722
0.6991	Remote Similarity	NPC476429
0.6991	Remote Similarity	NPC159815
0.6986	Remote Similarity	NPC473041
0.698	Remote Similarity	NPC472209
0.6978	Remote Similarity	NPC223242
0.697	Remote Similarity	NPC469452
0.6964	Remote Similarity	NPC478078
0.6961	Remote Similarity	NPC162694
0.6961	Remote Similarity	NPC230098
0.6957	Remote Similarity	NPC469450
0.6957	Remote Similarity	NPC230313
0.6952	Remote Similarity	NPC67904
0.6951	Remote Similarity	NPC477394
0.6951	Remote Similarity	NPC21638
0.6946	Remote Similarity	NPC282092
0.6943	Remote Similarity	NPC472121
0.6933	Remote Similarity	NPC74216
0.6923	Remote Similarity	NPC33256
0.691	Remote Similarity	NPC329932
0.6909	Remote Similarity	NPC77777
0.6901	Remote Similarity	NPC47059
0.6901	Remote Similarity	NPC329708
0.6901	Remote Similarity	NPC118832
0.6901	Remote Similarity	NPC165349
0.6901	Remote Similarity	NPC475147
0.6901	Remote Similarity	NPC264166
0.6901	Remote Similarity	NPC274291
0.69	Remote Similarity	NPC291173
0.6897	Remote Similarity	NPC469451
0.6897	Remote Similarity	NPC477395
0.689	Remote Similarity	NPC475559
0.6887	Remote Similarity	NPC473005
0.6881	Remote Similarity	NPC474745
0.6878	Remote Similarity	NPC37957
0.6878	Remote Similarity	NPC222046
0.6866	Remote Similarity	NPC35680
0.6866	Remote Similarity	NPC39822
0.6859	Remote Similarity	NPC473297
0.6857	Remote Similarity	NPC265642
0.6857	Remote Similarity	NPC218733
0.6857	Remote Similarity	NPC138615
0.6857	Remote Similarity	NPC132874
0.6856	Remote Similarity	NPC476220
0.6856	Remote Similarity	NPC160113
0.6851	Remote Similarity	NPC17437
0.6847	Remote Similarity	NPC97584
0.6847	Remote Similarity	NPC245741
0.684	Remote Similarity	NPC151171
0.6837	Remote Similarity	NPC53344
0.6837	Remote Similarity	NPC193238
0.6832	Remote Similarity	NPC474325
0.6827	Remote Similarity	NPC94499
0.6825	Remote Similarity	NPC280714
0.6824	Remote Similarity	NPC473540
0.6822	Remote Similarity	NPC268077
0.6818	Remote Similarity	NPC330009
0.6816	Remote Similarity	NPC126515
0.6816	Remote Similarity	NPC218594
0.6816	Remote Similarity	NPC99043
0.6816	Remote Similarity	NPC472331
0.6816	Remote Similarity	NPC274002
0.6812	Remote Similarity	NPC25401
0.6812	Remote Similarity	NPC22476
0.6804	Remote Similarity	NPC474058
0.6804	Remote Similarity	NPC477158
0.68	Remote Similarity	NPC168153
0.6797	Remote Similarity	NPC131977
0.6792	Remote Similarity	NPC329793
0.6792	Remote Similarity	NPC127178
0.6787	Remote Similarity	NPC126556
0.6786	Remote Similarity	NPC148124
0.6782	Remote Similarity	NPC237044
0.6781	Remote Similarity	NPC477066
0.678	Remote Similarity	NPC475981
0.678	Remote Similarity	NPC474746
0.678	Remote Similarity	NPC262725
0.6777	Remote Similarity	NPC100863
0.6777	Remote Similarity	NPC17677
0.6774	Remote Similarity	NPC475133
0.6769	Remote Similarity	NPC92191
0.6769	Remote Similarity	NPC230942
0.6769	Remote Similarity	NPC315498
0.6769	Remote Similarity	NPC59028
0.6766	Remote Similarity	NPC477393
0.6761	Remote Similarity	NPC471489
0.6761	Remote Similarity	NPC469732
0.6754	Remote Similarity	NPC470821
0.6752	Remote Similarity	NPC478082
0.6752	Remote Similarity	NPC478081
0.6752	Remote Similarity	NPC477067
0.6751	Remote Similarity	NPC472115
0.6751	Remote Similarity	NPC472114
0.6744	Remote Similarity	NPC470484
0.6743	Remote Similarity	NPC476651
0.6742	Remote Similarity	NPC470002
0.6742	Remote Similarity	NPC148183
0.6742	Remote Similarity	NPC470001
0.6742	Remote Similarity	NPC152768
0.6741	Remote Similarity	NPC99724
0.674	Remote Similarity	NPC248903
0.6738	Remote Similarity	NPC476258
0.6738	Remote Similarity	NPC304837
0.6733	Remote Similarity	NPC304675
0.6731	Remote Similarity	NPC203628
0.673	Remote Similarity	NPC66909
0.673	Remote Similarity	NPC302548
0.6729	Remote Similarity	NPC311357
0.6728	Remote Similarity	NPC205926

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 NPC474077 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	537
0.2-0.3	775
0.3-0.4	1749
0.4-0.5	2804
0.5-0.6	2548
0.6-0.7	551
0.7-0.8	5
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
0.7233	Intermediate Similarity	NPD6874	Approved
0.7053	Intermediate Similarity	NPD3812	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD6276	Discontinued
0.6984	Remote Similarity	NPD5811	Approved
0.6961	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7820	Phase 3
0.6901	Remote Similarity	NPD4122	Approved
0.6901	Remote Similarity	NPD32	Approved
0.6901	Remote Similarity	NPD4038	Approved
0.6901	Remote Similarity	NPD4034	Approved
0.6901	Remote Similarity	NPD31	Approved
0.6901	Remote Similarity	NPD4036	Approved
0.6901	Remote Similarity	NPD4033	Approved
0.6901	Remote Similarity	NPD4039	Approved
0.6901	Remote Similarity	NPD4035	Approved
0.6901	Remote Similarity	NPD4037	Approved
0.6875	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD8358	Approved
0.6845	Remote Similarity	NPD2843	Phase 2
0.6845	Remote Similarity	NPD2845	Phase 2
0.6842	Remote Similarity	NPD5582	Discontinued
0.684	Remote Similarity	NPD3416	Discontinued
0.6829	Remote Similarity	NPD4951	Discontinued
0.6823	Remote Similarity	NPD2672	Discontinued
0.6811	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD3983	Phase 3
0.6802	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4796	Discontinued
0.6771	Remote Similarity	NPD5617	Suspended
0.6769	Remote Similarity	NPD1742	Approved
0.6769	Remote Similarity	NPD1743	Approved
0.6769	Remote Similarity	NPD19	Approved
0.6766	Remote Similarity	NPD5313	Approved
0.6766	Remote Similarity	NPD5312	Approved
0.6759	Remote Similarity	NPD6296	Discontinued
0.675	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3453	Discontinued
0.673	Remote Similarity	NPD2974	Approved
0.673	Remote Similarity	NPD2973	Approved
0.673	Remote Similarity	NPD2975	Approved
0.673	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD4580	Approved
0.6713	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7546	Discontinued
0.6683	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD3965	Phase 1
0.6683	Remote Similarity	NPD5600	Discontinued
0.6682	Remote Similarity	NPD2494	Approved
0.6682	Remote Similarity	NPD3452	Approved
0.6682	Remote Similarity	NPD7476	Discontinued
0.6682	Remote Similarity	NPD3450	Approved
0.6682	Remote Similarity	NPD2493	Approved
0.6667	Remote Similarity	NPD7556	Discontinued
0.6667	Remote Similarity	NPD7811	Phase 3
0.6667	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4583	Approved
0.6667	Remote Similarity	NPD4582	Approved
0.6667	Remote Similarity	NPD7810	Phase 3
0.6651	Remote Similarity	NPD5871	Discontinued
0.6651	Remote Similarity	NPD2490	Approved
0.6651	Remote Similarity	NPD2488	Approved
0.665	Remote Similarity	NPD5557	Phase 1
0.665	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.665	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD683	Approved
0.6636	Remote Similarity	NPD6519	Phase 2
0.6636	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD3909	Discontinued
0.6633	Remote Similarity	NPD2821	Approved
0.6622	Remote Similarity	NPD3437	Discontinued
0.662	Remote Similarity	NPD4004	Approved
0.662	Remote Similarity	NPD4002	Approved
0.6618	Remote Similarity	NPD6184	Discontinued
0.6615	Remote Similarity	NPD3639	Approved
0.6615	Remote Similarity	NPD3641	Approved
0.6615	Remote Similarity	NPD3640	Phase 3
0.6604	Remote Similarity	NPD5548	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD2971	Approved
0.6602	Remote Similarity	NPD2968	Approved
0.66	Remote Similarity	NPD7315	Approved
0.66	Remote Similarity	NPD5183	Approved
0.66	Remote Similarity	NPD5186	Approved
0.66	Remote Similarity	NPD6071	Discontinued
0.6591	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD7565	Approved
0.6586	Remote Similarity	NPD8363	Approved
0.6586	Remote Similarity	NPD8364	Approved
0.6582	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD3656	Approved
0.6575	Remote Similarity	NPD4082	Approved
0.6574	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.657	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.656	Remote Similarity	NPD6905	Phase 2
0.6557	Remote Similarity	NPD7256	Discontinued
0.6552	Remote Similarity	NPD7797	Approved
0.6552	Remote Similarity	NPD7796	Approved
0.655	Remote Similarity	NPD2680	Approved
0.655	Remote Similarity	NPD2681	Approved
0.655	Remote Similarity	NPD6107	Approved
0.6544	Remote Similarity	NPD7497	Discontinued
0.6544	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3153	Approved
0.6538	Remote Similarity	NPD3154	Approved
0.6535	Remote Similarity	NPD7542	Phase 3
0.6535	Remote Similarity	NPD4481	Phase 3
0.6535	Remote Similarity	NPD3912	Discontinued
0.6534	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6238	Discontinued
0.6526	Remote Similarity	NPD5512	Phase 3
0.6525	Remote Similarity	NPD8016	Phase 3
0.6525	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD6625	Approved
0.6524	Remote Similarity	NPD5928	Phase 1
0.652	Remote Similarity	NPD7805	Phase 3
0.6516	Remote Similarity	NPD5860	Discontinued
0.6504	Remote Similarity	NPD7708	Approved
0.65	Remote Similarity	NPD2907	Approved
0.65	Remote Similarity	NPD2906	Approved
0.6492	Remote Similarity	NPD6666	Approved
0.6492	Remote Similarity	NPD6667	Approved
0.6488	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD2216	Approved
0.6485	Remote Similarity	NPD2970	Approved
0.6485	Remote Similarity	NPD2969	Approved
0.6485	Remote Similarity	NPD2215	Approved
0.648	Remote Similarity	NPD2789	Approved
0.6478	Remote Similarity	NPD7186	Phase 3
0.6476	Remote Similarity	NPD5558	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD3398	Discontinued
0.6468	Remote Similarity	NPD6457	Approved
0.6466	Remote Similarity	NPD7803	Approved
0.6465	Remote Similarity	NPD6063	Approved
0.6465	Remote Similarity	NPD3557	Approved
0.6465	Remote Similarity	NPD7600	Phase 2
0.6465	Remote Similarity	NPD3556	Approved
0.6465	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD2560	Approved
0.6465	Remote Similarity	NPD3558	Approved
0.6465	Remote Similarity	NPD5599	Discontinued
0.6465	Remote Similarity	NPD2563	Approved
0.6465	Remote Similarity	NPD5967	Approved
0.6465	Remote Similarity	NPD5071	Phase 2
0.6465	Remote Similarity	NPD3560	Approved
0.6463	Remote Similarity	NPD7955	Approved
0.6463	Remote Similarity	NPD7956	Approved
0.6462	Remote Similarity	NPD7296	Approved
0.646	Remote Similarity	NPD3354	Phase 2
0.6457	Remote Similarity	NPD7069	Discontinued
0.6456	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5429	Discontinued
0.6455	Remote Similarity	NPD7452	Approved
0.6455	Remote Similarity	NPD4596	Phase 1
0.6455	Remote Similarity	NPD7453	Approved
0.6449	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD8101	Phase 3
0.6442	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD5670	Approved
0.6439	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD3051	Approved
0.6435	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD5496	Approved
0.6432	Remote Similarity	NPD2238	Phase 2
0.6423	Remote Similarity	NPD8461	Discontinued
0.6422	Remote Similarity	NPD3057	Approved
0.6419	Remote Similarity	NPD4049	Phase 2
0.6418	Remote Similarity	NPD6746	Phase 2
0.6418	Remote Similarity	NPD6037	Discontinued
0.6414	Remote Similarity	NPD5772	Approved
0.6414	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD5773	Approved
0.6414	Remote Similarity	NPD6737	Phase 2
0.6414	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD6738	Phase 2
0.6414	Remote Similarity	NPD7599	Phase 2
0.6413	Remote Similarity	NPD4493	Discontinued
0.6413	Remote Similarity	NPD5676	Approved
0.6411	Remote Similarity	NPD6045	Phase 3
0.6408	Remote Similarity	NPD7479	Phase 2
0.6408	Remote Similarity	NPD5190	Phase 2
0.6408	Remote Similarity	NPD8492	Approved
0.6406	Remote Similarity	NPD4107	Approved
0.6406	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD4418	Discontinued
0.64	Remote Similarity	NPD4897	Phase 2
0.64	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD3006	Discontinued
0.6396	Remote Similarity	NPD4772	Phase 2
0.6396	Remote Similarity	NPD6386	Approved
0.6396	Remote Similarity	NPD6385	Approved
0.6396	Remote Similarity	NPD4773	Phase 2

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