NPASS Compound

Structure

CID247972 OpenBabel06191716052D 20 25 0 0 1 0 0 0 0 0999 V2000 -1.1242 0.3227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7775 0.4534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0692 3.0221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6315 0.7379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0692 1.0292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5728 3.1451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3564 1.7547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4656 2.0256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2063 2.5238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9934 -0.0240 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2063 1.5274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9322 2.5238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9322 1.5274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4337 1.7117 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6009 0.7915 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5728 0.9061 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5491 2.1643 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 2.8799 2.8318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8799 1.2195 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 3 9 2 0 0 0 0 3 12 1 0 0 0 0 4 10 1 0 0 0 0 4 14 1 0 0 0 0 5 11 2 0 0 0 0 5 13 1 0 0 0 0 6 9 1 0 0 0 0 6 17 1 0 0 0 0 7 15 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 10 1 1 1 0 0 0 10 20 1 0 0 0 0 11 16 1 0 0 0 0 12 13 2 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 16 1 1 0 0 0 14 17 1 0 0 0 0 15 16 1 6 0 0 0 15 20 1 0 0 0 0 16 2 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	269.11
Volume:	260.775
LogP:	1.864
LogD:	1.364
LogS:	-2.804
# Rotatable Bonds:	0
TPSA:	30.93
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.669
Synthetic Accessibility Score:	6.235
Fsp3:	0.5
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:	-4.8
MDCK Permeability:	3.599008414312266e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.269
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.907
30% Bioavailability (F30%):	0.135

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.996
Plasma Protein Binding (PPB):	72.02062225341797%
Volume Distribution (VD):	1.811
Pgp-substrate:	22.948856353759766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.822
CYP1A2-substrate:	0.645
CYP2C19-inhibitor:	0.864
CYP2C19-substrate:	0.838
CYP2C9-inhibitor:	0.182
CYP2C9-substrate:	0.369
CYP2D6-inhibitor:	0.965
CYP2D6-substrate:	0.842
CYP3A4-inhibitor:	0.935
CYP3A4-substrate:	0.769

ADMET: Excretion

Clearance (CL):	16.693
Half-life (T1/2):	0.62

ADMET: Toxicity

hERG Blockers:	0.25
Human Hepatotoxicity (H-HT):	0.29
Drug-inuced Liver Injury (DILI):	0.233
AMES Toxicity:	0.313
Rat Oral Acute Toxicity:	0.795
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.25
Carcinogencity:	0.909
Eye Corrosion:	0.005
Eye Irritation:	0.013
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC247972

Natural Product ID:	NPC247972
*Common Name:**	Apohaemanthamine
IUPAC Name:	n.a.
Synonyms:	Apohaemanthamine
Standard InCHIKey:	QMGIUGSXVRJVRE-LTTZEQNMSA-N
Standard InCHI:	InChI=1S/C16H15NO3/c1-2-16-11-5-13-12(18-8-19-13)3-9(11)6-17-7-15(16)20-10(1)4-14(16)17/h1-3,5,10,14-15H,4,6-8H2/t10-,14-,15+,16-/m0/s1
SMILES:	C1=C[C@]23c4cc5c(cc4CN4C[C@H]3O[C@@H]1C[C@@H]24)OCO5
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2087253
PubChem CID:	70693230
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004123] Crinine- and Haemanthamine-type amaryllidaceae 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
NPO4246	Brunsvigia radulosa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19533	Eucharis amazonica	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19533	Eucharis amazonica	Species	Amaryllidaceae	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
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	92900.0	nM	PMID[533107]

☑ 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 NPC247972 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	411
0.1-0.2	1490
0.2-0.3	5450
0.3-0.4	11793
0.4-0.5	9522
0.5-0.6	11101
0.6-0.7	2194
0.7-0.8	603
0.8-0.85	81
0.85-0.9	42
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9308	High Similarity	NPC475686
0.9308	High Similarity	NPC290759
0.9308	High Similarity	NPC266176
0.9308	High Similarity	NPC158148
0.9308	High Similarity	NPC82533
0.9308	High Similarity	NPC58766
0.9286	High Similarity	NPC78733
0.925	High Similarity	NPC474475
0.9193	High Similarity	NPC477640
0.9193	High Similarity	NPC225597
0.9193	High Similarity	NPC470739
0.9141	High Similarity	NPC474470
0.9057	High Similarity	NPC218614
0.9051	High Similarity	NPC215829
0.9051	High Similarity	NPC97072
0.9012	High Similarity	NPC75958
0.8938	High Similarity	NPC320104
0.8916	High Similarity	NPC244554
0.8889	High Similarity	NPC474324
0.8889	High Similarity	NPC57812
0.8889	High Similarity	NPC252960
0.8841	High Similarity	NPC65403
0.8834	High Similarity	NPC475845
0.879	High Similarity	NPC148898
0.878	High Similarity	NPC474708
0.878	High Similarity	NPC311991
0.8773	High Similarity	NPC181653
0.8773	High Similarity	NPC190332
0.8773	High Similarity	NPC100566
0.8662	High Similarity	NPC223125
0.8631	High Similarity	NPC15919
0.8625	High Similarity	NPC31311
0.8625	High Similarity	NPC234392
0.8623	High Similarity	NPC304675
0.8571	High Similarity	NPC237044
0.8563	High Similarity	NPC2314
0.8553	High Similarity	NPC223124
0.8553	High Similarity	NPC210148
0.8553	High Similarity	NPC233029
0.8535	High Similarity	NPC475959
0.8521	High Similarity	NPC474325
0.8519	High Similarity	NPC477080
0.8471	Intermediate Similarity	NPC474745
0.8447	Intermediate Similarity	NPC138487
0.8447	Intermediate Similarity	NPC216459
0.8447	Intermediate Similarity	NPC41178
0.8412	Intermediate Similarity	NPC148693
0.8412	Intermediate Similarity	NPC294790
0.8412	Intermediate Similarity	NPC118633
0.8395	Intermediate Similarity	NPC323443
0.8395	Intermediate Similarity	NPC147091
0.8395	Intermediate Similarity	NPC146288
0.8395	Intermediate Similarity	NPC180756
0.8373	Intermediate Similarity	NPC476002
0.8344	Intermediate Similarity	NPC130926
0.8324	Intermediate Similarity	NPC474746
0.8324	Intermediate Similarity	NPC475981
0.8323	Intermediate Similarity	NPC210918
0.8313	Intermediate Similarity	NPC231198
0.8313	Intermediate Similarity	NPC225774
0.8301	Intermediate Similarity	NPC7018
0.8294	Intermediate Similarity	NPC49353
0.8293	Intermediate Similarity	NPC92191
0.8293	Intermediate Similarity	NPC59028
0.8276	Intermediate Similarity	NPC9867
0.8266	Intermediate Similarity	NPC102760
0.8263	Intermediate Similarity	NPC476432
0.8263	Intermediate Similarity	NPC24264
0.8263	Intermediate Similarity	NPC219341
0.8256	Intermediate Similarity	NPC267408
0.8256	Intermediate Similarity	NPC126284
0.8242	Intermediate Similarity	NPC4304
0.8242	Intermediate Similarity	NPC249274
0.8229	Intermediate Similarity	NPC230098
0.8221	Intermediate Similarity	NPC76079
0.8221	Intermediate Similarity	NPC93593
0.8218	Intermediate Similarity	NPC156576
0.8214	Intermediate Similarity	NPC247389
0.8204	Intermediate Similarity	NPC180306
0.8204	Intermediate Similarity	NPC16805
0.8204	Intermediate Similarity	NPC302527
0.8204	Intermediate Similarity	NPC167546
0.8187	Intermediate Similarity	NPC37144
0.8187	Intermediate Similarity	NPC187678
0.8187	Intermediate Similarity	NPC59907
0.8182	Intermediate Similarity	NPC141440
0.8182	Intermediate Similarity	NPC237579
0.8182	Intermediate Similarity	NPC106786
0.8161	Intermediate Similarity	NPC248642
0.8161	Intermediate Similarity	NPC275132
0.815	Intermediate Similarity	NPC99179
0.8141	Intermediate Similarity	NPC314682
0.8133	Intermediate Similarity	NPC266753
0.8133	Intermediate Similarity	NPC232924
0.8133	Intermediate Similarity	NPC306902
0.8133	Intermediate Similarity	NPC160298
0.8133	Intermediate Similarity	NPC205167
0.8133	Intermediate Similarity	NPC477559
0.8107	Intermediate Similarity	NPC150879
0.8095	Intermediate Similarity	NPC276944
0.8095	Intermediate Similarity	NPC232514
0.8095	Intermediate Similarity	NPC238530
0.8089	Intermediate Similarity	NPC188163
0.8089	Intermediate Similarity	NPC213206
0.8089	Intermediate Similarity	NPC474915
0.8089	Intermediate Similarity	NPC328750
0.8086	Intermediate Similarity	NPC274026
0.8072	Intermediate Similarity	NPC111485
0.8057	Intermediate Similarity	NPC476575
0.8047	Intermediate Similarity	NPC124657
0.8036	Intermediate Similarity	NPC59567
0.8012	Intermediate Similarity	NPC51957
0.8012	Intermediate Similarity	NPC476144
0.8012	Intermediate Similarity	NPC16107
0.8012	Intermediate Similarity	NPC106295
0.8012	Intermediate Similarity	NPC210437
0.7989	Intermediate Similarity	NPC63152
0.7988	Intermediate Similarity	NPC168409
0.7988	Intermediate Similarity	NPC82285
0.7988	Intermediate Similarity	NPC133011
0.7987	Intermediate Similarity	NPC476567
0.7987	Intermediate Similarity	NPC128019
0.7987	Intermediate Similarity	NPC136860
0.7967	Intermediate Similarity	NPC14622
0.7967	Intermediate Similarity	NPC215098
0.7967	Intermediate Similarity	NPC124302
0.7967	Intermediate Similarity	NPC73020
0.7967	Intermediate Similarity	NPC46744
0.7967	Intermediate Similarity	NPC70290
0.7965	Intermediate Similarity	NPC149090
0.7965	Intermediate Similarity	NPC19520
0.7963	Intermediate Similarity	NPC7467
0.7955	Intermediate Similarity	NPC299990
0.7955	Intermediate Similarity	NPC233718
0.7955	Intermediate Similarity	NPC73492
0.7929	Intermediate Similarity	NPC233650
0.7929	Intermediate Similarity	NPC189470
0.7921	Intermediate Similarity	NPC214116
0.7914	Intermediate Similarity	NPC219162
0.7907	Intermediate Similarity	NPC6152
0.7904	Intermediate Similarity	NPC78359
0.7904	Intermediate Similarity	NPC148014
0.7904	Intermediate Similarity	NPC315707
0.7904	Intermediate Similarity	NPC65490
0.7904	Intermediate Similarity	NPC40389
0.7895	Intermediate Similarity	NPC298979
0.7892	Intermediate Similarity	NPC328700
0.7892	Intermediate Similarity	NPC202771
0.7892	Intermediate Similarity	NPC2173
0.7892	Intermediate Similarity	NPC119818
0.7892	Intermediate Similarity	NPC244112
0.7888	Intermediate Similarity	NPC185838
0.7886	Intermediate Similarity	NPC320223
0.7886	Intermediate Similarity	NPC114364
0.7882	Intermediate Similarity	NPC134858
0.788	Intermediate Similarity	NPC226652
0.788	Intermediate Similarity	NPC120671
0.788	Intermediate Similarity	NPC72788
0.788	Intermediate Similarity	NPC314100
0.7874	Intermediate Similarity	NPC229166
0.7874	Intermediate Similarity	NPC199465
0.7874	Intermediate Similarity	NPC128560
0.7874	Intermediate Similarity	NPC477558
0.7849	Intermediate Similarity	NPC241055
0.7849	Intermediate Similarity	NPC160570
0.7841	Intermediate Similarity	NPC220961
0.7836	Intermediate Similarity	NPC86144
0.7836	Intermediate Similarity	NPC304659
0.7834	Intermediate Similarity	NPC416184
0.7798	Intermediate Similarity	NPC129603
0.7798	Intermediate Similarity	NPC476572
0.7792	Intermediate Similarity	NPC160193
0.7791	Intermediate Similarity	NPC476151
0.7791	Intermediate Similarity	NPC321505
0.7791	Intermediate Similarity	NPC253883
0.7791	Intermediate Similarity	NPC90844
0.7791	Intermediate Similarity	NPC191376
0.7791	Intermediate Similarity	NPC95075
0.7791	Intermediate Similarity	NPC179825
0.7791	Intermediate Similarity	NPC210140
0.7784	Intermediate Similarity	NPC325871
0.7784	Intermediate Similarity	NPC99659
0.7778	Intermediate Similarity	NPC306669
0.7765	Intermediate Similarity	NPC24954
0.7751	Intermediate Similarity	NPC69360
0.7751	Intermediate Similarity	NPC118804
0.7744	Intermediate Similarity	NPC476571
0.7744	Intermediate Similarity	NPC135538
0.7744	Intermediate Similarity	NPC24233
0.7744	Intermediate Similarity	NPC428
0.7744	Intermediate Similarity	NPC130941
0.7744	Intermediate Similarity	NPC147390
0.7744	Intermediate Similarity	NPC246587
0.7735	Intermediate Similarity	NPC281581
0.7727	Intermediate Similarity	NPC241704
0.7727	Intermediate Similarity	NPC112575
0.7711	Intermediate Similarity	NPC476568
0.7711	Intermediate Similarity	NPC476579
0.7711	Intermediate Similarity	NPC326316
0.7711	Intermediate Similarity	NPC81733

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 NPC247972 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	665
0.2-0.3	905
0.3-0.4	2466
0.4-0.5	2627
0.5-0.6	1658
0.6-0.7	486
0.7-0.8	108
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8344	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD4584	Approved
0.7967	Intermediate Similarity	NPD4420	Approved
0.7953	Intermediate Similarity	NPD4481	Phase 3
0.7941	Intermediate Similarity	NPD6071	Discontinued
0.7937	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD2560	Approved
0.7904	Intermediate Similarity	NPD2563	Approved
0.7895	Intermediate Similarity	NPD2969	Approved
0.7895	Intermediate Similarity	NPD2970	Approved
0.7892	Intermediate Similarity	NPD5005	Approved
0.7892	Intermediate Similarity	NPD5006	Approved
0.7836	Intermediate Similarity	NPD3051	Approved
0.7831	Intermediate Similarity	NPD4772	Phase 2
0.7831	Intermediate Similarity	NPD4773	Phase 2
0.7778	Intermediate Similarity	NPD6107	Approved
0.7758	Intermediate Similarity	NPD4210	Discontinued
0.7746	Intermediate Similarity	NPD2489	Approved
0.7746	Intermediate Similarity	NPD27	Approved
0.7738	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD4236	Phase 3
0.7702	Intermediate Similarity	NPD4237	Approved
0.7614	Intermediate Similarity	NPD8156	Discontinued
0.7605	Intermediate Similarity	NPD4017	Approved
0.7598	Intermediate Similarity	NPD4578	Approved
0.7598	Intermediate Similarity	NPD4577	Approved
0.759	Intermediate Similarity	NPD3639	Approved
0.759	Intermediate Similarity	NPD3640	Phase 3
0.759	Intermediate Similarity	NPD3641	Approved
0.7568	Intermediate Similarity	NPD5582	Discontinued
0.7557	Intermediate Similarity	NPD8099	Discontinued
0.7557	Intermediate Similarity	NPD8251	Approved
0.7557	Intermediate Similarity	NPD8252	Approved
0.7527	Intermediate Similarity	NPD7906	Approved
0.7514	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5241	Discontinued
0.7485	Intermediate Similarity	NPD6030	Approved
0.7485	Intermediate Similarity	NPD6031	Approved
0.7473	Intermediate Similarity	NPD4663	Approved
0.7471	Intermediate Similarity	NPD7298	Approved
0.7468	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD2898	Approved
0.7442	Intermediate Similarity	NPD6788	Approved
0.7427	Intermediate Similarity	NPD2978	Approved
0.7427	Intermediate Similarity	NPD2977	Approved
0.7403	Intermediate Similarity	NPD2968	Approved
0.7403	Intermediate Similarity	NPD7313	Approved
0.7403	Intermediate Similarity	NPD7312	Approved
0.7403	Intermediate Similarity	NPD2971	Approved
0.7403	Intermediate Similarity	NPD7311	Approved
0.7403	Intermediate Similarity	NPD7310	Approved
0.7399	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7833	Phase 2
0.7399	Intermediate Similarity	NPD7831	Phase 2
0.7365	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7309	Approved
0.7346	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD4166	Phase 2
0.7326	Intermediate Similarity	NPD5773	Approved
0.7326	Intermediate Similarity	NPD5772	Approved
0.7318	Intermediate Similarity	NPD5312	Approved
0.7318	Intermediate Similarity	NPD5313	Approved
0.7308	Intermediate Similarity	NPD7280	Phase 3
0.7308	Intermediate Similarity	NPD7281	Phase 3
0.7288	Intermediate Similarity	NPD6687	Approved
0.7288	Intermediate Similarity	NPD6688	Approved
0.7278	Intermediate Similarity	NPD5976	Discontinued
0.7268	Intermediate Similarity	NPD8053	Approved
0.7268	Intermediate Similarity	NPD8054	Approved
0.7222	Intermediate Similarity	NPD2492	Phase 1
0.7219	Intermediate Similarity	NPD7296	Approved
0.7212	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3124	Discontinued
0.72	Intermediate Similarity	NPD5604	Discontinued
0.7196	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5718	Phase 2
0.7182	Intermediate Similarity	NPD3885	Approved
0.7176	Intermediate Similarity	NPD4727	Phase 1
0.7174	Intermediate Similarity	NPD6851	Approved
0.7174	Intermediate Similarity	NPD6853	Approved
0.717	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1424	Approved
0.7158	Intermediate Similarity	NPD2973	Approved
0.7158	Intermediate Similarity	NPD2975	Approved
0.7158	Intermediate Similarity	NPD2974	Approved
0.7152	Intermediate Similarity	NPD1375	Discontinued
0.7119	Intermediate Similarity	NPD5677	Discontinued
0.7112	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7149	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3109	Approved
0.7099	Intermediate Similarity	NPD3110	Approved
0.7098	Intermediate Similarity	NPD3450	Approved
0.7098	Intermediate Similarity	NPD3452	Approved
0.7093	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD2488	Approved
0.7074	Intermediate Similarity	NPD2490	Approved
0.7073	Intermediate Similarity	NPD6896	Approved
0.7073	Intermediate Similarity	NPD6895	Approved
0.7069	Intermediate Similarity	NPD3382	Approved
0.7069	Intermediate Similarity	NPD3384	Approved
0.7069	Intermediate Similarity	NPD3383	Approved
0.7051	Intermediate Similarity	NPD3705	Approved
0.7049	Intermediate Similarity	NPD6297	Approved
0.7047	Intermediate Similarity	NPD4580	Approved
0.7041	Intermediate Similarity	NPD7124	Phase 2
0.7039	Intermediate Similarity	NPD4010	Discontinued
0.703	Intermediate Similarity	NPD1753	Discontinued
0.7024	Intermediate Similarity	NPD6997	Phase 2
0.7017	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD2493	Approved
0.701	Intermediate Similarity	NPD2494	Approved
0.6983	Remote Similarity	NPD7802	Discontinued
0.6978	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2200	Suspended
0.6966	Remote Similarity	NPD7400	Phase 3
0.6964	Remote Similarity	NPD4162	Approved
0.6964	Remote Similarity	NPD3060	Approved
0.6959	Remote Similarity	NPD4107	Approved
0.6959	Remote Similarity	NPD5457	Discontinued
0.6959	Remote Similarity	NPD4123	Phase 3
0.6939	Remote Similarity	NPD4002	Approved
0.6939	Remote Similarity	NPD4004	Approved
0.6933	Remote Similarity	NPD3531	Approved
0.6933	Remote Similarity	NPD4475	Approved
0.6933	Remote Similarity	NPD3530	Approved
0.6933	Remote Similarity	NPD3532	Approved
0.6933	Remote Similarity	NPD4474	Approved
0.6923	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6748	Discontinued
0.6905	Remote Similarity	NPD7037	Approved
0.6904	Remote Similarity	NPD4582	Approved
0.6904	Remote Similarity	NPD4583	Approved
0.6898	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4005	Discontinued
0.6897	Remote Similarity	NPD7047	Phase 3
0.6895	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5978	Approved
0.6893	Remote Similarity	NPD5977	Approved
0.6884	Remote Similarity	NPD4859	Phase 1
0.6882	Remote Similarity	NPD3692	Discontinued
0.6879	Remote Similarity	NPD2122	Discontinued
0.6878	Remote Similarity	NPD7291	Discontinued
0.6871	Remote Similarity	NPD1336	Approved
0.6867	Remote Similarity	NPD6111	Discontinued
0.6867	Remote Similarity	NPD7119	Phase 2
0.6839	Remote Similarity	NPD3687	Approved
0.6839	Remote Similarity	NPD3686	Approved
0.6837	Remote Similarity	NPD4482	Phase 3
0.6832	Remote Similarity	NPD7827	Phase 1
0.6832	Remote Similarity	NPD7247	Discontinued
0.6824	Remote Similarity	NPD7466	Approved
0.6821	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD8095	Phase 1
0.6813	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5242	Approved
0.6808	Remote Similarity	NPD6625	Approved
0.6802	Remote Similarity	NPD3057	Approved
0.6791	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2161	Phase 2
0.6784	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD5160	Discontinued
0.678	Remote Similarity	NPD5720	Discontinued
0.6774	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7294	Phase 1
0.6765	Remote Similarity	NPD5177	Phase 3
0.6763	Remote Similarity	NPD2874	Phase 2
0.6763	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7020	Approved
0.6763	Remote Similarity	NPD7019	Approved
0.6761	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD4678	Approved
0.6761	Remote Similarity	NPD4675	Approved
0.6757	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3845	Phase 1
0.6734	Remote Similarity	NPD4040	Phase 1
0.6725	Remote Similarity	NPD6331	Phase 2
0.6725	Remote Similarity	NPD5754	Discontinued
0.6724	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6386	Approved
0.6723	Remote Similarity	NPD6385	Approved
0.6723	Remote Similarity	NPD1757	Discontinued
0.6722	Remote Similarity	NPD4055	Discovery
0.6722	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD3448	Approved
0.6717	Remote Similarity	NPD2972	Approved
0.6717	Remote Similarity	NPD3533	Approved
0.6707	Remote Similarity	NPD823	Approved
0.6707	Remote Similarity	NPD817	Approved
0.6706	Remote Similarity	NPD7153	Discontinued
0.6705	Remote Similarity	NPD2421	Approved
0.6705	Remote Similarity	NPD2420	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