NPASS Compound

Structure

CID24594 OpenBabel06191715352D 25 29 0 0 1 0 0 0 0 0999 V2000 -5.3816 0.2456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5535 -0.0748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2371 0.9715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5943 -2.5240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1200 -1.6733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5948 -2.4941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6462 -0.7927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5778 0.2262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6768 -1.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8480 1.1310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8480 -1.4107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5156 -0.2544 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1209 -1.6135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1804 -0.2544 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8506 -1.3764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8480 0.1310 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1804 -1.0253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6466 -0.7628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5778 -1.5059 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8263 0.0547 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9253 -0.3792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6525 -0.5087 0.0000 N 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 -2.9820 1.6310 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5156 -1.0253 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 13 2 0 0 0 0 7 18 2 0 0 0 0 9 15 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 1 1 1 0 0 0 12 16 1 0 0 0 0 12 25 1 0 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 14 8 1 6 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 15 21 2 0 0 0 0 16 10 1 6 0 0 0 17 11 1 6 0 0 0 17 19 1 0 0 0 0 18 23 1 0 0 0 0 19 9 1 1 0 0 0 19 22 1 0 0 0 0 20 8 1 1 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.22
Volume:	358.018
LogP:	3.25
LogD:	3.096
LogS:	-2.484
# Rotatable Bonds:	1
TPSA:	37.63
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.867
Synthetic Accessibility Score:	5.113
Fsp3:	0.619
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.272
MDCK Permeability:	1.2232114386279136e-05
Pgp-inhibitor:	0.981
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.135
20% Bioavailability (F20%):	0.701
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.84
Plasma Protein Binding (PPB):	69.03508758544922%
Volume Distribution (VD):	2.576
Pgp-substrate:	24.334556579589844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.169
CYP1A2-substrate:	0.618
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.953
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.287
CYP2D6-inhibitor:	0.701
CYP2D6-substrate:	0.903
CYP3A4-inhibitor:	0.042
CYP3A4-substrate:	0.881

ADMET: Excretion

Clearance (CL):	9.768
Half-life (T1/2):	0.281

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.495
Drug-inuced Liver Injury (DILI):	0.716
AMES Toxicity:	0.152
Rat Oral Acute Toxicity:	0.728
Maximum Recommended Daily Dose:	0.978
Skin Sensitization:	0.1
Carcinogencity:	0.592
Eye Corrosion:	0.006
Eye Irritation:	0.048
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC24594

Natural Product ID:	NPC24594
*Common Name:**	Macrocarpine B
IUPAC Name:	n.a.
Synonyms:	Macrocarpine B
Standard InCHIKey:	IYRQKBCVJYGVMJ-YCFPOQHFSA-N
Standard InCHI:	InChI=1S/C21H28N2O2/c1-12-16(10-24)14-8-20-21-15(9-19(22(20)2)17(14)11-25-12)13-6-4-5-7-18(13)23(21)3/h4-7,12,14,16-17,19-20,24H,8-11H2,1-3H3/t12-,14-,16-,17+,19-,20-/m0/s1
SMILES:	OC[C@H]1[C@H](C)OC[C@@H]2[C@H]1C[C@@H]1N([C@H]2Cc2c1n(C)c1c2cccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2332141
PubChem CID:	71720003
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003759] Macroline 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
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19191551]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	leaves	Purwodadi Botanical Garden, Indonesia	n.a.	PMID[20189404]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[22148233]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	Barks	n.a.	n.a.	PMID[23806072]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	bark and leaf	Pahang, Malaysia	n.a.	PMID[25211145]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28762	Alstonia angustifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	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	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	100000.0	nM	PMID[455627]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[455628]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[455628]

☑ 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 NPC24594 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	287
0.1-0.2	1353
0.2-0.3	7517
0.3-0.4	22527
0.4-0.5	5869
0.5-0.6	2657
0.6-0.7	1974
0.7-0.8	456
0.8-0.85	31
0.85-0.9	16
0.9-0.95	4
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472122
0.9812	High Similarity	NPC187827
0.9812	High Similarity	NPC472105
0.9691	High Similarity	NPC472110
0.9691	High Similarity	NPC472109
0.9451	High Similarity	NPC472108
0.9451	High Similarity	NPC139291
0.9325	High Similarity	NPC326575
0.9217	High Similarity	NPC472104
0.9152	High Similarity	NPC133261
0.8909	High Similarity	NPC472123
0.8882	High Similarity	NPC255229
0.8882	High Similarity	NPC81229
0.8869	High Similarity	NPC15840
0.8786	High Similarity	NPC469470
0.8786	High Similarity	NPC469501
0.8772	High Similarity	NPC79062
0.8772	High Similarity	NPC472107
0.8629	High Similarity	NPC472097
0.8626	High Similarity	NPC472111
0.8563	High Similarity	NPC472323
0.8506	High Similarity	NPC66210
0.8503	High Similarity	NPC317430
0.8497	Intermediate Similarity	NPC258480
0.8391	Intermediate Similarity	NPC472119
0.8304	Intermediate Similarity	NPC189812
0.8304	Intermediate Similarity	NPC329688
0.8242	Intermediate Similarity	NPC52557
0.8239	Intermediate Similarity	NPC62510
0.8229	Intermediate Similarity	NPC143533
0.8202	Intermediate Similarity	NPC175474
0.8192	Intermediate Similarity	NPC478077
0.8171	Intermediate Similarity	NPC113626
0.8152	Intermediate Similarity	NPC79129
0.8152	Intermediate Similarity	NPC195461
0.8152	Intermediate Similarity	NPC81654
0.8152	Intermediate Similarity	NPC313985
0.8152	Intermediate Similarity	NPC49196
0.8152	Intermediate Similarity	NPC249150
0.815	Intermediate Similarity	NPC121903
0.8132	Intermediate Similarity	NPC245916
0.8125	Intermediate Similarity	NPC19679
0.8107	Intermediate Similarity	NPC469541
0.8081	Intermediate Similarity	NPC158129
0.8066	Intermediate Similarity	NPC472113
0.8056	Intermediate Similarity	NPC472112
0.8054	Intermediate Similarity	NPC249040
0.8046	Intermediate Similarity	NPC203754
0.8046	Intermediate Similarity	NPC150048
0.8043	Intermediate Similarity	NPC50503
0.8	Intermediate Similarity	NPC234987
0.8	Intermediate Similarity	NPC211997
0.7978	Intermediate Similarity	NPC57994
0.7978	Intermediate Similarity	NPC289299
0.7976	Intermediate Similarity	NPC129721
0.7963	Intermediate Similarity	NPC20144
0.7956	Intermediate Similarity	NPC95783
0.7943	Intermediate Similarity	NPC134586
0.7937	Intermediate Similarity	NPC474145
0.7937	Intermediate Similarity	NPC475841
0.7861	Intermediate Similarity	NPC254240
0.7861	Intermediate Similarity	NPC128265
0.7861	Intermediate Similarity	NPC312870
0.7861	Intermediate Similarity	NPC294909
0.7861	Intermediate Similarity	NPC199851
0.7838	Intermediate Similarity	NPC472116
0.7812	Intermediate Similarity	NPC469589
0.7811	Intermediate Similarity	NPC285469
0.7778	Intermediate Similarity	NPC472294
0.7778	Intermediate Similarity	NPC104483
0.7772	Intermediate Similarity	NPC475422
0.776	Intermediate Similarity	NPC87755
0.7749	Intermediate Similarity	NPC238457
0.7746	Intermediate Similarity	NPC470508
0.7727	Intermediate Similarity	NPC52254
0.7705	Intermediate Similarity	NPC102338
0.7705	Intermediate Similarity	NPC111602
0.7705	Intermediate Similarity	NPC63199
0.7705	Intermediate Similarity	NPC196251
0.7701	Intermediate Similarity	NPC49954
0.7701	Intermediate Similarity	NPC474561
0.7701	Intermediate Similarity	NPC54988
0.7688	Intermediate Similarity	NPC311276
0.7677	Intermediate Similarity	NPC174788
0.766	Intermediate Similarity	NPC149708
0.7647	Intermediate Similarity	NPC207726
0.763	Intermediate Similarity	NPC194881
0.763	Intermediate Similarity	NPC16667
0.7622	Intermediate Similarity	NPC473763
0.7622	Intermediate Similarity	NPC117244
0.76	Intermediate Similarity	NPC160105
0.7586	Intermediate Similarity	NPC469813
0.7586	Intermediate Similarity	NPC78375
0.7586	Intermediate Similarity	NPC476446
0.7584	Intermediate Similarity	NPC472586
0.7574	Intermediate Similarity	NPC40070
0.7569	Intermediate Similarity	NPC233936
0.7561	Intermediate Similarity	NPC88097
0.7558	Intermediate Similarity	NPC469762
0.7557	Intermediate Similarity	NPC63751
0.7556	Intermediate Similarity	NPC472443
0.7549	Intermediate Similarity	NPC476492
0.7545	Intermediate Similarity	NPC472100
0.7529	Intermediate Similarity	NPC282231
0.7528	Intermediate Similarity	NPC314603
0.7528	Intermediate Similarity	NPC34508
0.7527	Intermediate Similarity	NPC159125
0.7527	Intermediate Similarity	NPC243716
0.7527	Intermediate Similarity	NPC472444
0.7514	Intermediate Similarity	NPC67056
0.7513	Intermediate Similarity	NPC165349
0.7513	Intermediate Similarity	NPC329708
0.7513	Intermediate Similarity	NPC47059
0.7513	Intermediate Similarity	NPC264176
0.7513	Intermediate Similarity	NPC118832
0.7513	Intermediate Similarity	NPC264166
0.7513	Intermediate Similarity	NPC274291
0.7512	Intermediate Similarity	NPC33949
0.75	Intermediate Similarity	NPC151939
0.75	Intermediate Similarity	NPC82070
0.75	Intermediate Similarity	NPC126066
0.75	Intermediate Similarity	NPC469785
0.7487	Intermediate Similarity	NPC476114
0.7487	Intermediate Similarity	NPC475910
0.7486	Intermediate Similarity	NPC21174
0.7486	Intermediate Similarity	NPC194640
0.7486	Intermediate Similarity	NPC40779
0.7486	Intermediate Similarity	NPC469938
0.7486	Intermediate Similarity	NPC271797
0.7475	Intermediate Similarity	NPC234078
0.7475	Intermediate Similarity	NPC469592
0.7475	Intermediate Similarity	NPC471080
0.7475	Intermediate Similarity	NPC471506
0.7475	Intermediate Similarity	NPC221100
0.7474	Intermediate Similarity	NPC102008
0.7473	Intermediate Similarity	NPC314394
0.7471	Intermediate Similarity	NPC279918
0.746	Intermediate Similarity	NPC231342
0.7459	Intermediate Similarity	NPC219336
0.7459	Intermediate Similarity	NPC248462
0.7458	Intermediate Similarity	NPC154293
0.7458	Intermediate Similarity	NPC201700
0.7449	Intermediate Similarity	NPC477548
0.7442	Intermediate Similarity	NPC470507
0.7436	Intermediate Similarity	NPC53344
0.7432	Intermediate Similarity	NPC163055
0.7424	Intermediate Similarity	NPC472098
0.7418	Intermediate Similarity	NPC300688
0.7418	Intermediate Similarity	NPC469896
0.7416	Intermediate Similarity	NPC280548
0.7414	Intermediate Similarity	NPC230869
0.7414	Intermediate Similarity	NPC221786
0.7414	Intermediate Similarity	NPC84508
0.7414	Intermediate Similarity	NPC474880
0.7413	Intermediate Similarity	NPC281049
0.7413	Intermediate Similarity	NPC469594
0.7409	Intermediate Similarity	NPC476874
0.7405	Intermediate Similarity	NPC474707
0.7403	Intermediate Similarity	NPC14325
0.7403	Intermediate Similarity	NPC183662
0.7403	Intermediate Similarity	NPC217372
0.7403	Intermediate Similarity	NPC28848
0.7403	Intermediate Similarity	NPC15573
0.7402	Intermediate Similarity	NPC475271
0.7384	Intermediate Similarity	NPC259644
0.7384	Intermediate Similarity	NPC73952
0.7384	Intermediate Similarity	NPC469763
0.7384	Intermediate Similarity	NPC469760
0.7384	Intermediate Similarity	NPC469765
0.7384	Intermediate Similarity	NPC25008
0.7384	Intermediate Similarity	NPC469786
0.7377	Intermediate Similarity	NPC71037
0.7374	Intermediate Similarity	NPC126492
0.7371	Intermediate Similarity	NPC229173
0.7366	Intermediate Similarity	NPC119700
0.7366	Intermediate Similarity	NPC204565
0.7363	Intermediate Similarity	NPC270009
0.7358	Intermediate Similarity	NPC475506
0.7354	Intermediate Similarity	NPC474177
0.7353	Intermediate Similarity	NPC21605
0.7351	Intermediate Similarity	NPC188387
0.7351	Intermediate Similarity	NPC163421
0.7345	Intermediate Similarity	NPC472106
0.7341	Intermediate Similarity	NPC80597
0.7341	Intermediate Similarity	NPC211572
0.7341	Intermediate Similarity	NPC70922
0.7341	Intermediate Similarity	NPC75540
0.7341	Intermediate Similarity	NPC212376
0.7341	Intermediate Similarity	NPC476219
0.734	Intermediate Similarity	NPC472099
0.7326	Intermediate Similarity	NPC173028
0.7326	Intermediate Similarity	NPC65215
0.732	Intermediate Similarity	NPC155143
0.732	Intermediate Similarity	NPC328596
0.732	Intermediate Similarity	NPC328318
0.732	Intermediate Similarity	NPC193761
0.7317	Intermediate Similarity	NPC198988
0.7316	Intermediate Similarity	NPC19692
0.7316	Intermediate Similarity	NPC220151
0.7314	Intermediate Similarity	NPC475990

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 NPC24594 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	524
0.2-0.3	590
0.3-0.4	1557
0.4-0.5	2676
0.5-0.6	2490
0.6-0.7	993
0.7-0.8	146
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8152	Intermediate Similarity	NPD4601	Approved
0.8152	Intermediate Similarity	NPD4600	Approved
0.815	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD4602	Approved
0.7872	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD4500	Approved
0.7861	Intermediate Similarity	NPD4501	Approved
0.7784	Intermediate Similarity	NPD7944	Discontinued
0.7771	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD4638	Approved
0.7759	Intermediate Similarity	NPD4640	Approved
0.7759	Intermediate Similarity	NPD4639	Approved
0.7746	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD2882	Phase 1
0.7735	Intermediate Similarity	NPD6227	Discontinued
0.7713	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD3385	Approved
0.7667	Intermediate Similarity	NPD8408	Discontinued
0.7661	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD5862	Discovery
0.765	Intermediate Similarity	NPD2383	Phase 1
0.764	Intermediate Similarity	NPD5104	Approved
0.7636	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD6158	Phase 2
0.7633	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD5899	Approved
0.7611	Intermediate Similarity	NPD5898	Approved
0.7611	Intermediate Similarity	NPD5897	Approved
0.7556	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD8021	Approved
0.7554	Intermediate Similarity	NPD8020	Approved
0.7543	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD2381	Approved
0.7542	Intermediate Similarity	NPD2382	Approved
0.7542	Intermediate Similarity	NPD2380	Approved
0.7514	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD4122	Approved
0.7513	Intermediate Similarity	NPD31	Approved
0.7513	Intermediate Similarity	NPD32	Approved
0.7513	Intermediate Similarity	NPD4034	Approved
0.7513	Intermediate Similarity	NPD4038	Approved
0.7513	Intermediate Similarity	NPD4033	Approved
0.7513	Intermediate Similarity	NPD4039	Approved
0.7513	Intermediate Similarity	NPD4036	Approved
0.7513	Intermediate Similarity	NPD4035	Approved
0.7513	Intermediate Similarity	NPD4037	Approved
0.7485	Intermediate Similarity	NPD4120	Approved
0.7485	Intermediate Similarity	NPD4121	Phase 3
0.7474	Intermediate Similarity	NPD7778	Approved
0.7474	Intermediate Similarity	NPD7777	Approved
0.7474	Intermediate Similarity	NPD53	Approved
0.7473	Intermediate Similarity	NPD6281	Approved
0.7473	Intermediate Similarity	NPD4203	Approved
0.7473	Intermediate Similarity	NPD4204	Approved
0.746	Intermediate Similarity	NPD7935	Phase 2
0.7458	Intermediate Similarity	NPD5021	Discontinued
0.7457	Intermediate Similarity	NPD4326	Phase 2
0.7449	Intermediate Similarity	NPD4520	Approved
0.7443	Intermediate Similarity	NPD2915	Discontinued
0.7442	Intermediate Similarity	NPD5743	Approved
0.7442	Intermediate Similarity	NPD5742	Approved
0.7442	Intermediate Similarity	NPD5741	Approved
0.7438	Intermediate Similarity	NPD3654	Approved
0.7419	Intermediate Similarity	NPD4334	Discontinued
0.7418	Intermediate Similarity	NPD6595	Phase 3
0.7396	Intermediate Similarity	NPD1683	Approved
0.7391	Intermediate Similarity	NPD4957	Phase 2
0.7389	Intermediate Similarity	NPD6492	Phase 2
0.7385	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD8063	Discontinued
0.7374	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD3002	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD4076	Approved
0.7363	Intermediate Similarity	NPD4079	Approved
0.7353	Intermediate Similarity	NPD4547	Phase 3
0.7353	Intermediate Similarity	NPD4702	Approved
0.7353	Intermediate Similarity	NPD4703	Approved
0.7351	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD5075	Discontinued
0.7351	Intermediate Similarity	NPD5555	Phase 1
0.7351	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7222	Phase 2
0.7337	Intermediate Similarity	NPD5596	Phase 2
0.7333	Intermediate Similarity	NPD750	Phase 2
0.7318	Intermediate Similarity	NPD1325	Approved
0.7318	Intermediate Similarity	NPD1326	Approved
0.7314	Intermediate Similarity	NPD5255	Approved
0.7308	Intermediate Similarity	NPD8122	Approved
0.7308	Intermediate Similarity	NPD8123	Approved
0.7308	Intermediate Similarity	NPD3505	Approved
0.7308	Intermediate Similarity	NPD3506	Approved
0.7294	Intermediate Similarity	NPD7469	Discontinued
0.7293	Intermediate Similarity	NPD5065	Approved
0.7292	Intermediate Similarity	NPD4397	Phase 1
0.7287	Intermediate Similarity	NPD4499	Approved
0.7253	Intermediate Similarity	NPD5100	Phase 3
0.7249	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD8114	Approved
0.7245	Intermediate Similarity	NPD8115	Approved
0.7243	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6285	Phase 2
0.7238	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7234	Approved
0.7234	Intermediate Similarity	NPD7233	Approved
0.7229	Intermediate Similarity	NPD45	Approved
0.7229	Intermediate Similarity	NPD6554	Approved
0.7228	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6452	Discontinued
0.7222	Intermediate Similarity	NPD7666	Phase 3
0.7222	Intermediate Similarity	NPD7665	Phase 2
0.7219	Intermediate Similarity	NPD4047	Discontinued
0.7213	Intermediate Similarity	NPD6159	Phase 2
0.7213	Intermediate Similarity	NPD2144	Approved
0.7211	Intermediate Similarity	NPD4315	Phase 2
0.7208	Intermediate Similarity	NPD7957	Phase 1
0.7208	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7483	Phase 2
0.7204	Intermediate Similarity	NPD7482	Phase 2
0.7202	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6026	Approved
0.7189	Intermediate Similarity	NPD3038	Discontinued
0.7188	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD8431	Approved
0.7167	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD6249	Phase 2
0.7165	Intermediate Similarity	NPD6248	Phase 2
0.7164	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5913	Phase 3
0.7151	Intermediate Similarity	NPD1661	Suspended
0.7151	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD6206	Phase 1
0.7143	Intermediate Similarity	NPD7418	Discontinued
0.7143	Intermediate Similarity	NPD6183	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD43	Approved
0.7143	Intermediate Similarity	NPD6182	Approved
0.7143	Intermediate Similarity	NPD7112	Discontinued
0.7136	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6978	Phase 2
0.7128	Intermediate Similarity	NPD5444	Phase 1
0.7127	Intermediate Similarity	NPD7474	Suspended
0.7122	Intermediate Similarity	NPD6455	Phase 3
0.7121	Intermediate Similarity	NPD7001	Phase 3
0.7121	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7271	Approved
0.7113	Intermediate Similarity	NPD6261	Phase 3
0.7104	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5140	Approved
0.7095	Intermediate Similarity	NPD5138	Approved
0.7087	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7453	Approved
0.7085	Intermediate Similarity	NPD7452	Approved
0.7081	Intermediate Similarity	NPD8386	Phase 2
0.7077	Intermediate Similarity	NPD6999	Discontinued
0.7077	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD3082	Discontinued
0.7071	Intermediate Similarity	NPD8272	Phase 2
0.7069	Intermediate Similarity	NPD4463	Approved
0.7069	Intermediate Similarity	NPD4462	Approved
0.7065	Intermediate Similarity	NPD5501	Discontinued
0.7062	Intermediate Similarity	NPD2581	Approved
0.7062	Intermediate Similarity	NPD2582	Approved
0.7062	Intermediate Similarity	NPD5003	Discontinued
0.7059	Intermediate Similarity	NPD2094	Phase 2
0.7059	Intermediate Similarity	NPD2092	Phase 2
0.7059	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5020	Approved
0.7059	Intermediate Similarity	NPD2095	Phase 2
0.7048	Intermediate Similarity	NPD7730	Approved
0.7048	Intermediate Similarity	NPD7731	Approved
0.7047	Intermediate Similarity	NPD4427	Phase 2
0.7035	Intermediate Similarity	NPD5530	Phase 1
0.7031	Intermediate Similarity	NPD6619	Phase 3
0.7031	Intermediate Similarity	NPD6569	Phase 2
0.7027	Intermediate Similarity	NPD4181	Approved
0.7027	Intermediate Similarity	NPD7111	Discontinued
0.7027	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD8326	Phase 3
0.7024	Intermediate Similarity	NPD8325	Phase 3
0.7021	Intermediate Similarity	NPD6178	Phase 3
0.7021	Intermediate Similarity	NPD2096	Phase 2
0.7021	Intermediate Similarity	NPD2091	Phase 2
0.702	Intermediate Similarity	NPD4886	Phase 2
0.7018	Intermediate Similarity	NPD3717	Discontinued
0.7018	Intermediate Similarity	NPD3525	Discontinued
0.7011	Intermediate Similarity	NPD482	Approved
0.7005	Intermediate Similarity	NPD6307	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4383	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